So having a section 8 tenant in there not only gives you difficulty with: showings, scheduling appraisals, removing tenants, etc, it also takes a way an extremely large buyer pool.Similar case for duplexes.

Of course, nothing is stopping you from selling Rental #1, paying taxes, and then taking your leftover after-tax profit and moving that into Rental #2. 

If you've lived in that house 2/5 years as your primary residence, you can also sell it tax free up to $250k single/$500k married-filing-jointly. 

A smart squatter will just figure out the drive-by schedule and move in afterwards....It will soon come to the point where we can never leave a house sitting vacant.....Did y'all ever think we'd even be having this conversation....? 

Here are some considerations and normal practices to ponder: Employee Structure, Contractual Agreements, Insurance Coverage Benefits, and HR MattersLegal and Tax ImplicationsCommunication  and Collaboration.

This sounds like a live in flip, which can be a nice way to get some tax free capital (if you live in it for two or more years).

Concurrently, I intend to construct our dream home on an adjacent 20-acre parcel that I already own outright.I've double-checked the property taxes, and they're not just accurate but slightly on the higher side.

@Ashish Acharya, @Basit Siddiqi, @Natalie KolodijThought that a single member LLC doesn't require a separate return and everything flows through to the 1040 Schedule E?

If you bought it for $450K and believe it is now worth $550K (get a realtor to confirm that), think about capital gains and taxes when you sell.  

I’m a 25 y/o Dentist in Canada, thinking of specialising in the US (2 year program) and live in the US afterwards.Any fellow Canadians here that can give me a general idea with tax/setting up corp and all for US RE journey?