Hi Wei Jie,The strategy can work as long as you have positive cash flow and deep reserves to sustain you through different cycles of the market.

@Byran Hyatt, great schools in East Lyme:https://www.trulia.com/p/ct/niantic/34-36-lincoln-...Deep River and Essex are also wonderful:https://www.trulia.com/p/ct/deep-river/91-w-bridge...https://www.trulia.com/p/ct/deep-river/10-high-st-...https://www.trulia.com/p/ct/essex/7-high-st-essex-...https://www.trulia.com/p/ct/essex/50-s-main-st-ess...https://www.trulia.com/p/ct/essex/55-s-main-st-ess...Schools aren't as good in Stonington, but it's my absolute favorite town in SE CT:https://www.trulia.com/p/ct/pawcatuck/63-moss-st-p...https://www.trulia.com/p/ct/pawcatuck/45-pawcatuck...

Some coops have flip or sale tax which if you ignore or miss can cut deep into your profit.2.

Thomas, we don't have deep pockets for deposits on homes.

@Alex Ko - it's a deep rabbit hole.

We're about 450 doors deep in Indy. 

One's tolerance--and desire--to navigate some of these issues stands to vary greatly based on whether it's a true labor of love or something you hope to hire out free of worries.With the cabin--before diving too deep into financial calculations--it would be good to get a clear assessment of its condition.

Seems to me that the deep pocketed Californian would be better off hard money lending than personally OOS investing in rental properties.

It is up to us to dig in deep, ask them the hard questions and learn everything we can about them BEFORE entering into a contract with them.

I am looking to learn as much as I can before jumping off into the deep end.