I'll just add that in addition to offsetting future tax liability, I'd like to offset current taxes as well, during my highest earning years. 

This can drastically reduce the property's value and cause unexpected headaches.I’m curious—what features do you prioritize when looking at short-term rentals?

Before I try to sell the idea to them I'd like to have the best data I can on potential earnings, upkeep costs, likely occupancy, and other points like that.

We certainly have found some deals that would reduce our living expenses compared to renting.

You have to earn a mentor by showing up a lot and then your mentor will appear.

Perhaps if your partner was a general contractor or handyman type there may be some merit there to reduce costs / increase profitability.If your partner enjoys deal sourcing, a better move might be for him to become an agent - so he could legally collect commissions from finding deals and managing properties for multiple people. 

My lease requires professional carpet cleaning, which would cost more than $500 for a home of that size.Yes, it's reasonable to reduce the cost because she was such a long-term tenant.

If you are skilled in each of the areas above, and you have enough in reserves to cover the costs of when things do not go as planned, then you can likely attract money from private money lenders who want to get a return on their money and they see lending to you as a low risk way of earning a better return than in the other passive investing options they have. 

After selling one and using a 1031 exchange to buy a fourplex in Chicago, he reduced his interest burden by 20% while boosting his net incomes by $1,500 per month.

If the Seller will not reduce the price to where it still makes sense to you then do not do this deal.