I also take an initial look at things like location dynamics (employment drivers, nearby schools/universities) and property condition.

Most agents will stop reaching out after 1-3 contacts but it'll take many more contacts to convert an expired lead who is getting dozens of weekly calls.To stand out, I would make your initial calls LESS about you and your value proposition and MORE about the lead themselves.Find out:- Why do they think the property didn't sell- What made them want to list the property in the first place (aka find out their motivation)- What is their "Plan B" if the property remains unsold in the next 6-12 months - If they're still interested in finding a buyer for their property AND how soon they'd ideally like to closeListen intently for any emotional cues (i.e. frustration, disappointment, hopelessness, etc.) and align yourself with them.

You can seek out contractors who work with lower initial deposits and work on net 30 payment periods.

For example: At the end of the year average stays should be 7 days or less for it to be an STR (IRS), host it yourself - do not use a property manager initially, materially participate in the STR (look up the 100 hr. and 500 hr. rule) - this total hour number is for you + spouse,  document ALL details on the work you are doing in the STR, do a cost seg on your property, use the cost seg to file for bonus depreciation - any STR property put into service in 2025 (after Jan 20) is eligible for 100% bonus depreciation (HUGE PLUS!).

However, new builds can have lower initial yields.Conversely, older properties are favored for maximizing yield, especially in high-demand areas, or by those willing to rehab.

We upgraded our website at a cost of about $2,000; we initiated a SEO program cost of which is $300 or so monthly, and we initiated an email campaign cost of $275 monthly.  

You're in the right place :) What strategy initially stands out to you, if any? 

Most policies "do" provide this protection, but some may exclude it or limit the amount of payout.Based off your initial question, your situation seems much more likely to be a maintenance issue, and not an insurance issue. 

My bookkeeper initially thought this was a weird setup but now has come to realize it’s super easy to keep track of income and expenses by individual property and to have instant access to a snapshot of how each property is performing.

I was doing 80% of the initial work only to get a 0% return.When that whole chaotic, unpaid effort sputtered out, I briefly tried to find a traditional career path again—anything to pay the bills and stop the real estate obsession.