While filings are a good thing to do for the optionee, they should not be free to cloud title without a detailed agreement or restriction.

Yes, a lease with rights to sub=let, an option and a seperate agreement for work to be done.I have no idea what Brian has as an addendum, but, an addendum is an addition to some basic agreement, if laws and custom restrict one from doing something under certain types of agreements, it's not a good idea to write another part of that agreement saying you can do that forbidden act!

I ask because there could be seller/ shorting lender restrictions on your ability to resell.Also, note to the other posters, Massachusetts convention is signing an offer to purchase, conducting inspections, and THEN signing a P&S.

It needs to address the functions but it should not be written so strictly or well defined that your by-laws or operating agreement becomes restrictive and requires modification to make a left turn.

Carrie Collyer - Your PM abilities were restricted because you were sending the identical message to multiple people.

You can convert an investment property to a primary residence and take advantage of benefits of the section 121 exemption for primary residences but there are limits, restrictions, and caveats. 

My main sticking point is that I am unsure how to find a marketplace that would be worth my time to find MFH properties effectively since I have minimal restrictions.

Caseworker will need to figure out the UAs and tenant's co-pay and maybe do a cursory inspection.If you mean you want an income-restriction on the property, I wouldn't do that.I guess the pros are that you get the voucher amount on the first and if the tenant becomes a PITA you can call the caseworker who can usually pull vouchers as enforcement.Cons are you'll prob be a little lower rent, you still need to collect the co-pay and the tenants (my own anecdotal observations) are tougher on the units. 

I have a feeling 12-18 months from now the lending restrictions wont be as strict. 

@Jesse Munos & @Stephan J Hagen - I've been bouncing around the idea of hosting, but with the COVID restrictions I'm pretty limited in options right now.