@Simon Delony Getting your spouse on board with real estate investing requires patience and alignment on financial goals.

If you want to combine two or more lesser sales into one higher purchase that is fine as long as your purchase meets the timing requirements for each sale.  

Hey Deirdre,To address your questions:Providing freedom by handling day-to-day operations.Offering peace of mind through proactive maintenance and tenant communication.Reducing risks by staying ahead of legal requirements, tenant screening, and dispute resolution.Enhancing the bottom line by identifying cost-saving opportunities while ensuring tenant satisfaction to reduce turnover.Is the experience still important when the property thrives financially?

They/you can't choose the carrier - their software assigns it.Fortegra is one of the carriers (paper in insurance parlance) that their product is written on.That said, Fortegra is A- rated I believe by AM Best so that isn't the issue.I'm going to take a guess and say that your umbrella is written with PersonalUmbrella.com (Markel) and they require all underlying insurance to be A-rated but also with an admitted carrier. 

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

Most hard money lenders require 10-20% down payment of the purchase price or total project cost.Holding Costs During Rehab: Yes, you'll need to cover carrying costs, including hard money interest, utilities, taxes, and insurance.

that isn’t subject to higher down payment requirements or higher interest.

If so I would thoroughly ready this to see what they require and what you agreed to.I doubt you can keep your permit if you refuse their inspection.If you are doing everything as you should, you shouldn't have anything to worry about.

As I see it, the only ways that real estate pays you well in the first 3-5 years is low to no leverage or a strategy that requires more work (short term rental, mid term rental, rent by the room, etc.).  

So I’m trying to come up with a game plan  Conventional loans do require 25% down on an investment property.