Will be far easier to purchase more property with 10% downpayments vs 20-25% for each one.Umbrella insurance isn't too expensive, $2M for $1200 per year.Just be sure to run the properties as a good business, address any concerns brought up by the insurance company (they usually do annual inspections). 

Most of the loans I do are on 25 to 30 year amortization, and included in that is people calling me b/c their current bank would only do 15 or 20 in cases where they've had the property for 15 or 10 years already.Every time your car insurance is up for renewal, that's an opportunity to make the carrier earn, or re-earn, your business.

My career before REI was as an IT project manager at an insurance company.

Not only would you benefit from having a partner's input on the deal, but you would also have an experienced individual to work alongside with as you navigate the project.It's also important to make sure you have identified your "team" ie; contractors / realtors / lenders / insurance agents / title company / etc. 

Home values have been rising, and you may reach this amount sooner than you think. 2. can you lower your homeowner's insurance?

He told me that the only time in his 30+ years that the scammer paid off is when the crook unexpectedly died and had a large life insurance policy that was able to pay off all the creditors.

Yes, talk to your Insurance Co.

Make sure you know your exact insurance costs with a specific STR policy that has general liability as well.

Life insurance might be another untapped source of liquidity to look into (if you have one in place).

Inspection Costs - $400 Lender Fees - $1,000 Closing Costs - $2,000 Mortgage Payments - $2,500 Property Taxes - $600 Utilities - $1,000 Insurance - $200 Commissions - $4,000 Selling Closing Costs - $4,000 Home Warranty - $500 Termite Letter - $100 MLS Fees - $100