While the economics are not as favorable for you, raising $300-$400k to buy something like a 1.2mm property will be far easier than trying to raise $10mm to buy a 100 unit.  

If you offer more $ for the property than the all cash offers AND you appear to the seller to be highly qualified in the method you are using for sourcing the payment, at some point your offer will be more appealing than the all cash offers.I don't understand why you would consider a 1031 for another property in two years. 

Add Hurricane Ian and you're not making anything easier or more timely. 

This appeared to be everything I was missing.

A smaller paid off portfolio seemed a lot easier to manage so that is the path I was on.. but I've come to the realization if I ever want to accumulate serious wealth I will have to use leverage and scale big. 

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

I can assure you that the more you learn regarding these products, the easier it is to help all of your clients.

Investors that will go say 250 to 1 mil or more once you prove your experience are far easier to deal with and the only ones I personally interact with.

However, an easier option would be to use a bridge loan to help with acquisition and rehab financing if the property needs some work.

An easier route would be to convince him to go in on the short term rental together in a partnership.