I would raise his rent to $500-has a garage-biggest disadvantage for perceived value for me is the smaller kitchenTHEORETICAL RENTERS INFO-two friends of mine who are getting married are very interested in renting my current property if I get a new property.

I can see how accumulating multiple 2 to 4 unit properties could end up with the disadvantages of both Single Family(not much economy scale) and Multifamily(dealing with a lot of units).

What are the advantages or disadvantages?

That person" but everyone who's just following prompts in turbo tax type software I'd bet dollars to Doughnuts I can find at least one mistake, tax disadvantage, missed deduction, ect. 

Permitting gives contractors control of the project and I have seen bad contractors use that control to the disadvantage of the investor,Regarding your last few comments about crews, a good PM should have crews relieving the investor of that problem.

At least in DFW area you will likely be at a disadvantage if trying to buy 2-3-4 plex with FHA. 

What are the advantages for both sides and what are the disadvantages? 

For the life of me I can’t figure out the advantage or disadvantage of an LLC if you don’t have any employees.  

If I rent thru LLC and sell after an year, does that then make it disadvantageous to do it with S-corp?

Think about what you would not like about running a hotel and make sure a STR doesn't have those same disadvantages.