One strategy is to pursue properties (in your preferred markets) that have been listed for sale for over 90 days (even longer is better).

Ensure your contractor has a clear timeline, keep extra cash reserves, and start marketing your rental rooms early. 

But, the self-sufficiency test for FHA loans can be really difficult in SF, meaning that the market rent from units you will not occupy must be sufficient to pay for the mortgage payment. 

However, I made the decision when interest rate was lower and there was support for an appreciating real estate market.

Fairmont is a good little market!

==========================My relative is asking if this is a viable way to legally avoid having to pay taxes:STEP 1: SELL PRIMARY RESIDENCE (House A)-Sell primary residence to son-in-law for cost basis + $500K-File gift tax form for difference between sale price & market value-Not pay capital gains on $500K due to personal exemption.STEP 2: SELL RENTAL PROPERTIES-Do 1031 exchange and buy House A back from son-in-law-Rent out House A for 1 year before move back in==========================Thoughts?

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

My easiest, no hassle, lowest expense rentals are the ones where the tenants stay 5 + years, do minor maintenance themselves, call me immediately with any issues so I can fix them before they become much more costly, and agree to annual market adjusted rent rate increases.  

Your realtor will be able to give you a much more detailed market specific answer but with house hacking and a VA loan it should be possible to get 0 out of pocket.

You should start with a focus on a 2 unit multifamily property in a market that you can afford to get into.