Being a remote location might already limit client base.

With the limited info, I would say #1 is your smartest option but there are a lot of variables missing.

I currently assign these scores manually, but it’s tedious and limits how quickly I can evaluate opportunities.Ideally, I’d like to:•Automate the collection of MLS/Zillow data.

I would recommend considering conventional financing until you reach Fannie Mae's limit of 10 properties, then consider either a portfolio loan, and start your race to 10 again, or look at DSCR at that time. 

Actually the IRS does not tell us what we can invest in, only what is disallowed (life insurance contracts and collectibles).Allowable investments for SDIRA investing include the following:Residential real estate, including: apartments, single family homes, and duplexesCommercial real estate Undeveloped or raw landREITs (Real Estate Investment Trusts)Real estate notes (mortgages and deeds of trusts)Promissory notes Private limited partnerships, limited liability companies, and C corporationsTax lien certificatesOil and gas investmentsPrivate stock offerings, private placementsJudgments/structured settlementsGold bullion Factoring investments

Ourcurrent approach involves identifying possible contact information for thelisted owners and calling multiple numbers, but this process is time-consumingand yields limited results.

Quote from @Jonathan Greene: That's very limited information for someone to help you.

So, that makes a BIG difference in How you scale and what your personal “upper limits” are.  

you might say something like, "I’ve been studying Austin and Denver for rental properties and have a $200,000 price limit—what are the pros and cons of both markets?"

Hi Marc - Aircover offers some protection for damages caused by guests, but it’s limited and doesn’t replace having dedicated STR insurance.