As is much of the US right now, Southern Vermont is undergoing some extreme weather right now.

Hi Account Closed,My first question would be if the property is currently undergoing probate.

Is there a lot of deep fat frying taking place in the home?

The barriers to entry for being an attorney are quite high (undergraduate degree, LSAT entrance exam, admission to law school, successful completion of law school, pass the bar exam, undergo fitness of character investigation).  

@Vickiel WoodardFirst, congratulations on taking some VERY positive steps under difficult personal situation.I would guess from your post that you have some expenses to incur for repair, rehab and carrying costs, before you begin receiving income.If your intent is to hold as rentals for good cash flow, a fix n flip type lender (where most SFR investor lending is available), will probably not be interested unless they believe you plan to sell after rehab.As you stated, you won't qualify for a conventional or institutional loan, not only because of credit but also because of loan size.The suggestions made by posters so far are some version of(1) sell as is one, two, or all(2) sell one and use proceeds to fix up other twoNot bad advice, depending on your goals.These lower end houses will sell for a VERY low price in relation to their rental income because (1) tenant types will most likely be a problem or at least be high maintenance, i.e. chasing them for rent, high turnover, life crisis, employment problems, etc, and (2) unless area undergoes gentrification price increases will be non existent (3) effective outside property management is probably not available.So, if you are able and willing to manage the property and tenants yourself, keeping the properties as cash flow rentals can be a VERY lucrative activity.I would find an experienced contractor, and talk him into either (1) partnering with you by providing his services as a contribution for buying an equity interest in the houses or (2) accepting a lien on the properties in lieu of immediate cash payment to perform the necessary rehab and either making monthly payments to him to pay off the lien once the units are rented or paying him off by refinancing once the properties are rehabbed and income is established, though as mentioned a loan would be somewhat difficult to accomplish.An alternative is to attend your local REIA meeting, and discuss a partnership with some of the more passive investors.BTW, are you paying typical credit card interest rates of 12-24%, or did you get an introductory deal giving you a low or no interest loan for 6 -12 months?  

I know this is the obvious, whatever you do if there is not enough fat in the deal just give it a miss. 

My worry is that someone just made a mistake and I’m going to have a fat bill come tax time, or this will eventually bite me.

I was the stocky (fat) bald guy walking around handing out business cards on steroids. 

We take in high volumes of reservations and our properties undergo excessive wear and tear due to holding 15-25 people at a time and having revolving stays.

That takes out the high end flips and the big fat juicy margins I hear about, but it provides us with a comfort level.