But, when you combine all the potential lost income and damages, I will definitely be the losing party since there's a cap on small claims.

I suppose I could combine the two ideas and live in a basement while renting out a 2 bedroom home to a traveling agency. 

Most won't entertain STR arbitrage.

I'm Francisco Centeno (REALTOR)So, cost segregation is basically deducting the depreciation of a property for years.Now, in the hypothetically situation...If both of you combines were earning $700k and you just bought a $2m property, and the cost segregation you got from a professional for the $2m property is $316k.

I can only speak to the Texas market, where malls that focus on creating consumer experiences (coffee shops, kids play area, entertainment-based tenants) are still performing well even in this age of online shopping.  

I was in a similar position a few years ago, but fortunately got married and our combined incomes helped us qualify for a larger house hack.We're on our second one in NOVA, Alexandria to be exact, and instead of rent by the room, we are renting out our walkout basement on Airbnb to monthly guests.That said, we have a number of friends doing well with rent by the room across NOVA, though they're purchasing homes with 5+ rooms or finding homes that can be renovated to include that setup.I'd recommend attending meetups such as the one I cohost, NOVA REI or Cashflow Breakfast Club or any of the others to meet those who are house hacking.

@Katie Miller, I purely entertain referrals from other people who have had great experiences with niche CPAs. 

A friend of mine invested in one last year—apartments upstairs, a small coffee shop downstairs - and the combination of income streams made it a steady performer.Scaling with a 1031 Exchange:While not applicable unless you sell a property, planning for a 1031 exchange could help you scale quickly while avoiding capital gains taxes.

I have three listings, 1. unit with a pool and hot tub, 2. unit with a hot tub, 3. both units together as a 12 sleeper.Gross monthly income (after booking channel fees) for the first unit over a 7 month period was $7309.Gross monthly income for both units over a 14 month period is $11,297 (after booking channel fees) As a long term rental the combined rent would be in the region of $5500.Is it possible to sell the property based on the income generated by the STR business or would the value always be based on bricks and mortar comps? 

This is Subject-To.We can make it more complicated by combining some elements of these different financing strategies.