And could even get a second home loan if doing traditional financing.

I still have that house and it rents for a grand these days. my first house was late 70s that I bought  in those days it was 80 10 and 10  you need 10% cash and normally a private HML would give you the 10% second and bank was the first.. interest on the first was 9% second was 15%.. this was before the Carter interest rate run up.. paid 80k for it in Milpitas CA.. and it was brand new bought it from Shapel . 

For the second, by "trying" I don't mean that we're struggling to do that but I see why it comes off that way.

(Previous rent was $1,300 but we're about to put in a brand new kitchen from the studs, new flooring throughout the house, new furance, adding A/C, etc).So do we just pay for it all upfront and mostly drain all of our savings, or do I let the rent pay for it and utilize our other savings to get a second property this spring/summer to increase our cashflow? 

on second thought your numbers are fairly conservative.

The second DOS was in 2020 when I bought enough properties using "subject to" that I couldn't keep up with rehabbing and some sat for a couple of months.

Mexicos second largest revenue source are wired funds from the U.S. by individuals.  

Second, most tenants are lucky they can dress themselves in the morning, much less paint walls without destroying the floors, ceiling and trimwork.

Update: the second deal just failed with complete loss of all investments.

yea i would say no. if you are second guessing it. doesnt see much benefit to you mainly them. but stay on good terms