But I would recommend cutting out the middle men.

Hello Lesley, Have you thought about using a DSCR loan to do a cash out or rate and term refinance to recoup the out of pocket money you have spent on the property.

@Joshua DunlapRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

I already own rentals out of state.

Very expensive markets have the problem that when they get too expensive, they price people out of the market so they move. 

Please feel free to reach out should you have more questions.  

I currently own a townhouse in Natick with a low mortgage rate and am considering buying another home to move into for 2-3 years, then probably renting it out.

There is no requirement to have your rental in an LLC to rent out your old home. 

At this stage in my investing career I don't buy things that don't cash flow, so if the fixer upper is going to bleed cash until it's fixed, I wouldn't invest in it. 

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