I was mostly looking for a multi-family in downtown Troy to occupy and house hack, but the local market is hot right now, it seems highly speculative, and at the end of the day the properties are 100+ years old, many needing extensive masonry work, etc.My realtor ended up showing me a HUD property in Rensselaer / East Greenbush area - a 2 bed, 1.5 bath townhouse built in 1988.

you have alot of needs and requirements. not a bad thing, but makes it difficult. first, it's Sofia, not Sophia (the name)second, those countries are 2nd world countries and it's always risky and speculative to buy there, i dont care who you are. the craziness and inflation in the late 90's and early 2000 is long gone and the prices have leveled off.I'd never buy there for "investing", i'd buy to live only hoping that one day it would appreciate. 

I consider this type of investment more speculative and when their is a boom there is eventually a BUST !

I'm tired of speculating and guessing in my own head.

But flipping is a specific business - and the most successful professional flippers over cycles don't hold inventory to "speculate" on further upward appreciation.

My investment plan is all about cash flow not so much speculation and appreciation.

What's the difference between speculating future (continued) market appreciation vs. buying in the PRE-GENTRIFIED areas because "it looks" like that's where the attraction is headed? 

Which is money I can use on more 'speculative' properties that might not cashflow as well.

The biggest problems that investors/speculators deal with are:Defining riskManaging riskDeveloped processes and proceduresExecuting the planTo many new investors/speculators focus on activities that have nothing to do with investing, market behavior...

That's not investing...that's speculation.