A 10-15 year return on a multifamily property in Boston will create life changing wealth and will obliterate returns from other, cheaper markets.

LLC will not save you taxes.This post does not create a CPA-Client relationship.

It seems to me that any addendum signed later after the initial lease may create a messy situation. 

For example, population growth in certain neighborhoods and increased investor activity have created opportunities for both long-term rentals and value-add deals.If you’re torn between wholesaling and holding long-term rentals, I’d suggest thinking about your long-term goals.

As @JonathanGreene said, tech has created an environment that allows folks like you Jon, to enjoy investing on your terms so that you do not put all of your eggs into one basket (so-to-speak).

@Dustin Horner you should be contracting maintenance work and creating a preferred list of vendors as @Phillip Austin has recommended.The first person you hire to help you should be to handle what you LEAST like to do yourself or has the greatest time savings for you!

Disallowed losses under wash sale rules increase the cost basis of replacement securities, potentially reducing future taxable gains.This post does not create a CPA-Client relationship.

Once you're ready, create a goal (e.g., "I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it.

For rentals, consider holding properties in an LLC for liability protection.This post does not create a CPA-Client relationship.

What I wrote above does not create an attorney/client relationship between us.