The ability to effectively self manage would depend on the scale you are trying to buy. 

This is a family property for which I will be paying 3/4 of the most recent assessment value.

Also , I would love to connect with any agents who specialize in STR market in Boston Mass area. airdna is pretty accurate . lenders use it to assess rental comps for short terms rentals when financing a short term rental  I use it for DSCR loans as well; it is accurate yet conservative because it gives you the median 50 percentile for the area based on comps.

If maintaining cash flow is your primary objective, you might want to explore other options.

This is a family property for which I will be paying 3/4 of the most recent assessment value.

Reward: Assess whether the uncertainty surrounding the current occupants, title clarity, and liens aligns with your risk tolerance.

We are looking to move from that, to a rental property, or a self storage property.Hey @Steve Wortman, welcome to the BP Forum!

Also be aware of Unrelated Business Income Tax (or UBIT) on leveraged real estate inside of an IRA.Or better yet, since you are self-employed - go with a truly self-directed Solo 401k plan, which would be a much better option and will help you avoid the UBIT on this investment.

Quote from @Johnny Lynum: Quote from @Billy Smith: I like SFH in the A-B area rent it you do the  upkeep  doing as much as possible your self to help max your rent out .I like to pay down the note as fast as possible .If in a C-D area I would flip the SFH wash your hands of it.SFH are generally easier to unload if you get in a cash crunch, I like staying in the first time home buyers level of a SFH  keeping it in a hot zone .If I were a BIG fish I would do deals at various level's of course after  doing the home work . 

@Steve EnglehartGet your retirement funds into a self directed IRA.