I wanted to cash in on the equity and trade up to a larger property.Purchase price: $1,250,000Cash invested: $50,000What made you interested in investing in this type of deal?

I think you're making the right move here to address this in a proactive manner as opposed to reactive when the problem is larger. 

It can be scary when you think about the larger numbers, but just keep in mind, they're just numbers.

Buy one larger deal at $1.6 mil with ????

At this point in time, I can't justify investing there when I can deploy slightly larger amounts of capital at a comparable price to rent ratio in parts of the SF Bay Area. 

So the investor chose to not keep all liquidity tied up in one property, cash out & convert to a rental instead.

That pertains to buying more real estate especially an investment property that requires reserves and a DP that comes form a liquid reserve unless the lender allows for the use and the calculation of DTI with the new payment is within approved ratios.

Business products that that scale to larger amounts are Buildium, Appfolio and ManageCasa especially for someone with less 50 units, since the entry price is pretty low and they include maintenance management.

Even in my market it'll differ on size:  Airbnb comprises most of the smaller sized units but it flips to vrbo as unit size gets larger.

Given you had 250,000 liquid why wouldn’t one:1) Purchase a 3 Bedroom 2 Bath Condo2) Rent out two rooms for 900 monthly each 3) Take the third room “effectively removing your rent payment you will need anywhere”Result - 2700 x 12 = 32,400 minus 10,000 for HOA and Yearly Property taxes.