TravelPhotographer

Receiving ~$100K+ settlement related to intellectual property infringements, which will count as 2016 income, I assume. Need to invest all business-wise, to reduce taxes on it, by end of 2016. Any strategy involving greatest amount of NYC
lodging nights is possibility, say, numerous 4-wk stays over next decade -- all tax deductible business trips. Alternative: paying a chain in advance for nights anywhere chain offered. Mid-level 3* preferred so #total nights maximized. Do any hotels-chains offer pay-up-front-get-discount rates?
Any advice appreciated! ^ ^ ^

Yoshi212

You should talk to your accountant and strongly consider that advice. You may be able to offset some of the tax liability with business expenses but if done incorrectly you could end up with business expenses without the balanced benefits of reduced tax liability.

sonofzeus

OP: you want to shelter (not convert) the income. Pay a good CPA for his intellectual property/advice. It will be worth every shekel in the short and long term.

TravelPhotographer

Further explanation:
self employed full time travel shooter ~28 yrs,
so all travel-related expenses are deductible;
expecting more pre-court settlements in coming
years, seeking hotel & airline offers that involve
advance lump sum payments towards future
(mid-level) lodging & (busn) flights; one way might
be to buy huge amounts of points-miles but am
seeking better deals than that scheme, if they exist?
Hoping advanced** travelers will advise. Thanks!

**advanced in the intricacies of hotel & airline programs,
which I am not...

Kagehitokiri

do agreement / contract with sales manager (or owner of hotel)

certain number of nights, per year, or total, at certain rate (like corporate rate)

note independent hotels can be better / more flexible than big chains

TravelPhotographer

Thanks, but independent hotels have higher chance of folding,
declaring bankruptcy, changing ownership, deteriorating, etc...?

Yoshi212

Purchasing points as a person is usually not a great value (there are exceptions and bonuses do make them more attractive) but I'm thinking maybe gift cards would be a better way to go. Be sure to check fees/expiration requirements.
Some airlines have/had accounts you could store money in. I think United may have carried over the CO Travel Bank in some form. Once again be sure to check for any fees or expiration requirements.

I still think this is in general not the best use of your settlement money. A good CPA can reduce your tax liability with high benefit to you.

Long Train Runnin

An AA AAirpass maybe?

Kagehitokiri

no different from chain hotels, and youre talking lower level chain franchises

even if a chain hotel is owned by the chain (small percentage) they can sell anytime

independent boutique (and even luxury) hotels sometimes cost less than big chains

TravelPhotographer

That's the kinda thing I might be seeking!! ^ ^ ^
Any kinda AA AAirpass forum on flyertalk??**
Wonder if any hotel chains offer same kinda scheme...??
regards

**http://www.flyertalk.com/forum/ameri...thread-29.html

sdsearch

Not a separate forum for AA AAirpass of course, it would be just a thread in the AA forum, which it look like you found already.

I seem to recall UA having something similar, but I don't remember its name.

Hotel programs are different than airlines. Airlines own their fleets; hotel programs don't own their hotels. For this reason, when you're paying an airline you're paying the airline itself. Even when you book a hotel on the hotel program's website, most of the money is going to the (usually independently owned) hotel.

The only equivalent I've thus seen at hotels is travel cards and hotel gift cards, BUT: They're a pain to redeem, because the hotel has to do all sorts of processing on each one to redeem it. And since I don't think they're available in high denominations usually, that could mean handing a whole stack of them to the hotel and the hotel needing an unreasonable amount of time to process them all.

Marriott used to sell gift cards at grocery stores and such, but discontinued that a few years ago. They may still sell them online, I dunno, but again I doubt they sell any with enough value for a 4-week stay in one card. And thus processing headaches of handing the clerk a giant stack of cards upon arrival for one stay.

You can still buy Southwest gift cards at grocery stores, but again they're limited in how much each card can hold, so to use a lot of money you'd have to buy a lot of gift cards.

(The only hotel I used to see consistently on grocery store gift card racks was Marriott. The only airline I consistently still see on grocery store gift card racks is Southwest.)

gardener

Is your business on the cash method or accrual method?

I would open a Solo 401(k) and put the max in there. It is over $50K.

Kagehitokiri

looking at numbers not percentages, there are chains that own a fair amount

more importantly, there are owners who own many across multiple chains

negotiating x nights at x rate is going to beat most 'gaming' methods

Efrem

Aside from this, which is usually true, every program I'm aware of has annual limits on how many of these one person can buy. These limits are too low to make buying airline miles/hotel points a useful strategy here.

manneca

Get tax advice. Or you risk having your scheme (in the British sense) fall apart.