@Patrick HancockLLC's are not free and there are costs associated with LLC1) Formation costs - potential attorney fees and setup fees with the state2) Registered agent fees if the LLC is not in the state that you operate out of3) Annual fees to keep LLC active4) Bank feesThere are also additional administrative burdens with having so many LLC's.

Are you looking to invest out-of-state or keep it local? 

. - Back everything about your financial plan into that end state. - NOW, run your draft plan by a CFP or three. 

Compare that to mature vacation rental markets in your home state of Maine (as a random example).

It is landlord-friendly, and specific pockets have gone upwards of 2-4x in the last 5-10 yearsA ton of MTR/LTR opportunities for out-of-state investors.

The size of the house is pretty typical of a lot of county guidelines. 200 extra SQFT is not that big a deal IMHO.The property is a zoned SFR1 or whatever the New York state zoning codes are.

With second home loans, the mortgage must be for one unit (I do a lot of 2-4 unit STRs), the property must not be rented for more than 180 days out of the year (limits revenue), must function reasonably as a second home (usually limits out of state investing), rental income will not qualify as stable monthly income (projected AirDNA does not play into your DTI).

I live in the Pacific northwest (central Washington state).

In other words, fewer lawsuits but harder ones.Multifamily - Many of the issues you mention vary widely depending on the state where you do business

Which state do you want to invest it makes a big difference