Are there any good ways to monetize points?

I'm not talking about selling awards, but redeeming awards for business travel in lieu of putting in for a reimbursement.

I have stayed at rates where I would have preferred to use points than charge the client, provided I got the money. I didn't bother with it because I wasn't sure how to do this.

In particular, I have a lot of hotel points.

Any suggestions?

I've tried this before. Someone at my company needed to fly to wherever on fairly short notice. Fares for the particular times that were needed came up to about $1200 roundtrip. For fun, I checked award availability and found a coach seat on exactly the flights needed (very surprising to say the least). Since I happened to be a little short at the time, I offered to sell the company 25,000 miles for $900. They did consider it, or at least they said they did. As it turned out, the travel plans fell through about as quickly as they'd originally materialized.

I've since in our travel policy something regarding use of points being forbidden for company travel. You may accrue them, of course, but it looked to me like they were specifically trying to prevent people from using their points and then being reimbursed the cash equivalent.

YMMV

Tax consequences are probably complicated to figure out. For tax purposes, spending miles has no taxable value. So the IRS considers you got the flight for free. If your employer then gives you $900 in lieu of buying the ticket for you, you've made $900 which would be subject to income tax, etc.

My compay offers an option to book a ticket with your miles, and in exchange the travel department will pay you 50% of what the ticket would have cost.

I did this once with a consulting client (after checking). They were happy to pay an invoice with documentation of what a paid ticket would have cost. It was taxable, of course, because it wasn't offset by an expense.

My company provides business class tickets for travel over 4 hours. I once bought an upgradeable Y fare on a transatlantic flight and used miles to upgrade it. I then had the company reimburse me for the "replacement" of the miles at the rate the airline charged to purchase miles. Total cost to the company, including the Y fare, was still well below the cost of a business class ticket.

Last year, I booked an award ticket for a business trip to California. I did not submit for any kind of reimbursement, but on my taxes I put $300 towards "performing artists/teacher/etc. expenses", as $300 seemed a fair and a easily verifiable price for a what a ticket from DFW-SFO would cost (unless you happened to get a good sale for maybe $220/250). I ended not being able to claim the performing artist expenses anyway, though, since I only had one W-2 from a performing arts company last year and not the minimum of two as required by the IRS rules (I think). In hindsight, it wasn't a good thing to try in the first place, and I won't do that again.

my question goes to how one submits the reimbursement. I guess the best practice is to have a conversation with the payor in advance to disclosse what you are doing, and then somehow come up with a fair quote for the current cash going rate. I'm industrious, so the second part is easy. Its the awkwardness of discussing this with the payor where I would appreciate suggestions. Good point about employers not wanting to get involved due to tax reporting issues.