There is quite a bit of upfront education you will need, but that's no different from active investing - you will definitely have much less to do after your investment.In my experience as an active investor, unless you have a solid advantage - market knowledge, skills with a hammer - you won't beat the returns of passive real estate syndications where you have a professional asset manager handling your investment. 

Considering that few tenants climb up on the roof and tear off the shingles, or take sledgehammers to the units, you would still be looking at a reasonable profit over time if all of your catastrophe came true. 

The whole world knows that NY has gotten hammered hard, or are your tenets telling you to screw off because you can’t evict?

We could theoretically go much higher if we weren't handling the maintenance, but the nature of maintenance in properties like these is that I ALWAYS have to be available, and when the hammer comes down I have to be able to devote many hours to a problem at once, often at a moment's notice.

I think commercial RE is going to be the canary in the coalmine for the sector.However, I also am not crazy about getting hammered with capital gains taxes if I don't have anything to 1031 into. 

I do have stocks but I wasn’t thinking that I should play the market but if the stock market keeps getting hammered, then I could see myself waiting to get some blue chips as the time to buy is when there is “blood in the streets”.

You may not need to go in swinging hammers yourself but there may be some minor things you can do to make your property more appealing to tenants.

I would be covered if there is a problem and it costs me $100 a year.Keep hammering on AirBNB to stand by their guarantee.

I am ready to scale but know I need to hammer down solid financing and taxes but struggling with where to begin.

Part of this depends on whether you'd like to do any work yourself - with the 203K you need a licensed contractor to complete the work and can't break  out your hammer much yourself. 3.