How cheap it is kind of makes me think they should be thrilled with everything as is.

Hate to echo all the wise responses above, but it does sound like you're setting yourself up to be a potential distressed foreclosure statistic the next time prices start dropping or your good neighbourhood goes bad (and thinking it can't happen is not being optimistic, it's pure gambling).Keep renting until you can afford better, or even keep renting period, and invest in real investments, as opposed to the home you want to be living in - you can rent that home easily enough, with no big dramas occurring if you're suddenly stressed for cash for whatever reason, and have to downscale - you simply move to a smaller place in that case.The criteria for the home you want to live in and the good investment you want to purchase are completely different - often contradictory.

Therefore, I am uncertain as to how much I can profit, and therefore, I am on hold.I would say that if you already had Portfolio of buildings like mine which had properties acquired decades ago and had already captured a large amount of Appreciation where the Price may move down a bit, then it's worth keeping for the Gamble that the future politics may not touch 2 to 4 Family Buildings.So for me personally, I am keeping the portfolio but am not expanding it.What I will expand, however, is my Property Management business should the future regulate my buildings!

This is a 1 bedroom condo that does not make sense to rent out.Purchase price: 390kRehab:  30kCurrent value: 485kWhen I say 485k, I mean that if I put it on the market for that price today then it would have 10 offers for that price within a day.So the main question is:Do I sell it now and pay the higher taxes on the sale, or do I gamble with waiting till October to avoid paying capital gains taxes?

Going in debt to invest is gambling.

These are the normal people in society.Those that decide to gamble savings do so with the understanding that they are risking it all by starting.

He is very thrilled with a program called Contract Collector.

I am wondering how much of a gamble I'd be taking because negative monthly cash flow seems pretty risky.

It was a gamble/"fun money" buy for us both as he is brand new to real estate and just wanted to get his feet wet and it was in a market I was a little curious about.

Gambling is everywhere now and already much closer with Philly under an hour away compared to NYC at two and half.Hotel room occupancy and food/beverage numbers are strong here.