Also be wary of wholesale and fix and flips that may have adverse tax consequences and need to be insulated in their own separate tax person (corporation) to avoid propagating to your other passive activities.

Honestly I can't imagine trying to pay off most mortgages in increments when you could simply put the cash to more work elsewhere, unless maybe if the house was already very close to being paid for.I suppose also if you were very risk adverse and wanted to build equity in the property for a refinance later on to reduce payments... but given that interest rates are not going to get any lower (foot in mouth perhaps) I would hesitate to plan to refinance later on to increase cash flow.So the long and the short of it is, it depends, but it seems likely to best scenario would be to refi the high interest rate items and use the cash gain to pay off the near-complete items (or use the capital you're planning to use in 'safe' higher paying investments for a set period and then cash it all out at once).

Some ResourcesHOW TO INVEST ‘SUBJECT TO’ AND OVERCOME THE “DUE ON SALE” CLAUSE | EREI 28BP Radio Podcast 002: Starting Out with Karen Rittenhouse – Subject To, Direct Mail, and Investing from a Woman’s PerspectiveBP Podcast Show 70 buy subject-to, with wrapped mortgage, selling owner financed

Great job @Kim Handelman with persevering through unseen adversity to close the deal.  

He likes the area b/c there are tons of service jobs, plus a number of colleges in the vicinity whose employees would have a hard time purchasing in Fairfield County, so the rental market is a vibrant one.I can't speak to flips in Bridgeport specifically, but as a general rule I figure if you price it right and make sure the monthly payment appeals to most buyers, that's how you overcome the high tax issue.

I think having a down payment of 20% or more is one barrier I will have to overcome.

I've even gotten title to props via adverse possession.

It is great to hear where people have come from, their challenges, and how they have overcome them.

Each deal is different and how you structure the deal depends on the problems you need to overcome.

How have you overcome any financing issues as a non US citizen or resident?