so the time issue is critical alluded to by Dave foster ??

@Dave Foster is a 1031 expert and may wish to chime in.BTW---they don't have to be similar.

@Brie Schmidt and @George Foster host a pretty good one up North not too far from you.

@Dave Foster @Rob Beland  (apologies, the links don't work on my internet)Thanks for your input folks, learning a lot here about 1031s.

Shane, I'm new to BP but wanted to share your site fosters engagement.In addition to you having your own blog for educating people and driving traffic....One of the fastest and first ways you can use to drive traffic to your site is to build relationships with other real estate investor blog owners and offer to contribute good educational content for their audience to - "guest post" on their blogs.

Your gain/loss isn't based on what you owe on the house It's going to be your sale price - (your purchase price + any improvements made)= gain/loss You're also going to have depreciation recapture at 25%Also though regarding a 1031. 1) Yes you can 1031 into more than 1 property to hit the equal/greater requirements 2) You have to match debts on the properties, I'm not sure that you could do a hard money loan up front vs. a traditional loan- @dave @Dave Foster would know3)  You should likely talk to an accountant or do some research into how the gain/loss on a sale of a rental is calculated and how 1250 tax comes into play 

@Dave Foster Ah...

There are several schools in my area that teach it, but I found that the broker Long & Foster teaches it for the lowest price.

Thanks @Dave Foster!!

The returns in my 2nd Scenario with a 20% down payment and 80% LTV is just about what I normally do and the Appreciation Rates is a little bit higher than what you achieved from 2007 to today.An example would be a property I bought in Clinton Hill Brooklyn in 2004 for $890k is now worth $3 Million today.A second example is a property I bought in Bed-Stuy Brooklyn in 2014 for $900k, renovations of $375k, now worth over $2 Million.I've done this 8 times consecutively and by intelligent decision making.I think that you can look at certain up and coming neighborhoods in NYC that are primed for future appreciation where you can still buy in should you decide to house hack it.I included David Foster in this posting because I think one of your option is to do a 1031 exchange into another property if you feel your area is currently peaking.