I have not ruled anything out at this point.

I've never really dealt with this scenario first-hand (and I don't ever plan to), but I do talk with a lot of tax delinquent sellers who have back due HOA fees - and just for the sake of expanding my knowledge of how this relationship works, I'm trying to fully understand any/all consequences that come when a property owner violates HOA rules like this.

I'm looking to pickup more buy & hold properties and seems like I have to go west of Worcester, MA to get respectable cash flow (near the 2% rule) or (12+% cash on cash w/ some leverage).

But one never knows how the court will rule.

What do you think the opinions would be of most Realtors who got a license and are trying to play by the rules?

Schedule E helps of course.Verify the gross incomecalculate the property taxes that you will pay when the property is re-assessed after the saleGet a few new insurance quotes because it normally increases for new owners if your lender requires windstorm coverageAdd a management feeuse the 50% rule to quickly look at deals to estimate a cap quickly

By Matt's logic and the 1/100 rule, in theory, I more than doubled my chances for a successful deal.

The rules are probably different everywhere I guess.

Since you mentioned the expected cash flow of your house, I'd encourage you to look into various perspectives regarding the 50% rule.

. $76k is already considered a debt against you regardless if you use it or not.Say you use another $20k from your $76k to buy a second property, the same rule as above applies.