@Brian Ewell One pretty common strategy is filling up those loans in the conventional bucket and then refi into a commercial loan (blanket loan) where you can package 4-8 properties into one loan.

So my life is sort of on hold until I can check this item off of my bucket list. 

Yes, knight in shinning armor and a rust bucket shister later on.I learned that one too, if they can't make the PITI, it's doubtful they will continue to make the PITI at a higher rate plus rental cash flow.I'd look closely as to why the got in trouble, like medical bills or job loss, if those issues have passed it may work, if not, expect problems ahead. :)

do hard money charges fee's up front with no guarantee they will fund... but from what I hear they do fund deals for some folks.. so just know that you could lose 3 to 4k using them .. those numbers are pretty stunning seems to me you could find a local cash partner and just split profits.. that's what I would do to start filling up your money and experience bucket

From there you will have to put the financiers into buckets based on what your capital needs are.

If this project were going to be 10 years it would be a different story but in respect to a Million dollar investment, 18 months is a drop in the bucket for most. 

The only bucket of capital where this wouldn't be the case would be with a bank, who will typically have an in-house team processing the loan and boiler plate loan language.

Even if I do have to pay gains on the sale and can't do a 1031 exchange... if I sold, I would just reinvest in another piece of real estate to generate another bucket of losses to keep my gains tax free. 

I'm sure it has not been easy.This post struck me as I just finished reading about 5 months ago a book which said something to the effect of- "If you come to me and ask me how to invest 500k I'll tell you to go invest in yourself first"Real-estate isn't as simple as dropping cash in a bucket and watching it grow, it's very intricate.

I'm jealous 😊 Hawaii is on my bucket list to visit.....some day🤔