What challenges are you anticipating on Oct 3 this year when TRID is supposed to be implemented? 

If you are working one property at a time and buying right and not only spending 6 months you probably aren't going to get stuck - most likely the worst thing that could happen would be that you would lose the anticipated equity you are building.

If the same happens to your husband and you're both out of work for much longer than you anticipated, your situation will be even tougher.

While we anticipated some repairs in our offer price, the inspection has revealed some more significant issues with the slate roof (expected) and the brick and chimneys (less expected).  

On top of that, he said our house cost him $4,000 more than what he originally anticipated, which was over 20% of our contract price.

Credit Score 795, so i don't anticipate a problem there.

from Alperlaw.comOne practical limitation with the multi-member LLC or partnership charging lien protection is that the debtor’s cash and assets can remain trapped inside the entity as a “patient creditor” holds its charging lien anticipating future distributions.

What I've been doing is some quick math on a spreadsheet - throwing in the taxes, anticipated rent, and some percentage based costs (10% vacancy, 10% maintenance, etc).

So, before you contract, you need to work backwards, find the market value of the property in good marketable condition, then start subtracting the costs of repairs, holding costs anticipated, transaction cost and desired profits to get to your buy price. 

However, in a big snow I anticipate needing someone to clear the sidewalk and do some alley clean-ups since the City can ticket the Owner the sidewalks are not shoveled.