My hesitation is that because this is winter and this is a new vendor, we would be paying the vendor an extra $275 per month for however many months left in winter, and the new vendor would then "owe" us the additional service calls. 

My goal is two-gold:  1st to provide cash flow to reinvest and grow my wealth and 2nd to provide me some extra money to enjoy with my family.

I am in the same boat and having difficulty

For an extra step of protection, we do have an insurance policy on each lockbox just in case, however, we have never had to use it.I hope this helps! 

However, these are not forms that you can print yourself– they have to be ordered from the IRS and take weeks to be mailed to you (assuming there are no extra delays from a government shutdown).The least hassle is to submit your 1099s to the IRS online, however not directly with the IRS.

I would think that having a cashflowing property with little (or hopefully zero) capital tied up would only help with fixing your credit (via extra cashflow to pay off debts) and get you in a better position for the next move.

We have a relative with extra cash who is willing to loan us money for the rehab.

So now I'm pondering taking that extra and saving up a down payment for my first property. 

I'm at the point where I'm interested in using my military retirement plan (TSP) to offer a cash deal on a property that is a two for one with extra room to build an additional small property, in a very busy, close to base location. 

How difficult is it to get into tax liens?