If they try to pay their labor as 1099 they run at great risk of violating a host of draconian labor laws such as AB5, the borello law and a litany of "misclassification" laws.There are substantial differences in how "right to work" statstate as operate as opposed to "non right to work" states.SBA defines a small business based on employees and revenue size.

Purley asset-based lenders are most likely going to be hard money lenders whose rates are typically going to be much higher.

Not sure how old you are, and $200K in a 401K may be a little or a lot based on age, there may be so many implications taking out money from your $401k, especially if you are still working for this company.feel free to reach out for tax advice

This allows you to invest in the locations that offer the best ROI and make the most sense based on your goals where you can be a bit more passive in your investment property.

There are way better people to talk to that are based out of here and know the market like the back of their hand. 

The reason you would hire a licensed professional is to assist with you not gettting SCAMMED and help you with negotiating prices and terms...based upon State Law. 

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.

I would only underwrite based on actual rents not proforma.

Dwelling (Building coverage)The limit should be based on the Replacement Cost of the building (cost to rebuild withthe same kind and quality excluding the foundation)2.

I'm now based in Ohio, specifically Cleveland, where properties range from $100K to $300K.