I suppose we could all cheer you on and give you advice on how to "10x" your goals and flip 20 houses this year and purchase 30 investment properties, but that's like encouraging someone to jump off a 30-foot diving board after watching them belly-flop in a kiddy pool.You have one rental that has fallen apart and eaten up your cash.

The only consistent positive reviews I've heard from the likes of Zillow are from those who are spending 5 figures per MONTH.Better to work your sphere and do belly-to-belly marketing and networking. 

Suggest a belly to belly meeting with the Seller, Bill, and Kevin to talk.

There’s your estimate.In most of my syndications the taxable income has been near zero in the first couple of years (we do cost seg so that juices it but even without cost seg the taxable income should be fairly low thanks to standard depreciation).  

YOU could find success in either route but it depends on the fire in your belly to succeed and how determined you are to put in the work to make it work. 

However, you may have a hard time finding a seller who will take second lien because they potentially end up with nothing (not even a property) if your financial situation goes belly up. 

You'll have a difficult time finding an investor who went belly up while owning property in cash.  

But you must be able to demonstrate your intent.So in your case selling a portfolio of rentals to buy one really juiced beautiful property to hold as a rental is fine for 1031. 

You should have seen the belly laugh.. at the time that county was so poorly run that titles would take on average 90 days to record .. so they had to offer gap insurance which was the first time I learned of this little nugget..

When you send out blind offers, you'll get more interested sellers calling you (not the other way around), and you'll close more deals.Just an idea to get your creative juices flowing.