Bottom line is condos having HOAs and special assessments simply can not cash flow.

If you're not buying up to the maximum you can qualify for you should be fine.If you'd like to be in a ready position you could always get your credit, income, and assets reviewed and planned for in advance, because a loan is basically compromised of those three areas.LIke Chris mentions above though, if you buy a property that positively cash flows using the formula of 75% of gross income minus your mortgage payment per month (PITIA - principal/interest/tax/insurance/assessments)  = a positive number then "yes," your DTI will go down each time you buy another property.

Perhaps a General Contractor can come in for an repair "assessment" and can look for other damage related to the property, well, and septic tank, and give you some estimate advice.

Examples include a sports store (in a hockey/baseball town), a gym, a deli and a dozen others. 2.

SEAN - I am a HML and I have BRRd a dozen or so low end properties over the years.  

You should come and visit the Bay of Fundy coast sometime and you might alter that assessment.   

How would you ever have any hope of assessing properties without looking at them?

You'll then be able to have tax advantage there.There could be other advantages regarding your situation and the desired legal structure you want.Also, you might want to consider other variables such as:S-corp tend to necessitate more paper filing and upkeep The way you're going to get funding might be different with S-corpAs always, you'll need the help of professionals to assess your situation. 

Totally agree with your assessments of this market, and not to mention these large mutual fund buyers who pay retail price for foreclosure properties.  

Make sure you have a good grasp on historical HOAs and assessments.