Quote from @Eric Huntermark: Additionally, as I'm thinking about conventional loan products as well.

However, Allstate is capping their landlord insurance at $750,000, which creates a coverage gap I need to address.I’m looking for options to add at least an additional $750,000 in coverage and am wondering if anyone has experience with Difference in Conditions (DIC) coverage or Excess and Surplus policies.

Could be the tenant is not using the service, doing something to attract roaches or the exterminator isn't doing their job.

What would be my best route to take if we need additional finances?

I have seen all sides of this equation, self managing my own properties locally, but moved with the Navy 1000 miles away and managed the same rentals from afar, and had friends here in Memphis that had 18 properties and had them all with PMs with varying levels of success, some bad and some great.Self-managing brings about an additional level of responsibility that most of the time is fine, but that is not what you hire a PM for.

I agree with the others here that say you need to have some skin in the game, if you are going to live there yourself, get an FHA loan rather than owner financing, you can get a 3.5% down loan, personally I do not love these as they require  PMI which is an additional expense, and you also need  bring additional funds for closing at least for taxes, title, attorney and transfer fees . borrowing from anyone else for the down payment, to include a personal loan from the bank is not a good idea, those again will be higher int. rate.

I pull permits for removal of load bearing walls, addition of bathrooms or bedrooms, addition of footage.

Part of considering acquiring a property should include additional possibilities.

Could I instead hire foundation repair and soil stabilization services to prevent foundation issues?

Here's an article with additional FAQs on cost segregation studies that you may find helpful.