I have never painted brick but I would think the hardest part would be to get good coverage...you’d need a really fluffy roller to get the mortar joints.

I saved $629 per year on one property by switching from Allstate to Safeco:Dwelling coverage $76,500 Liability $300,000Safeco $486  (.6 % of insured value) vs Allstate $1115Heres my new agent for anyone interested, shes great to deal with:Jodi FirestoneLanders Insurance1424 Sherman Ave #400, Coeur d'Alene, ID 83814

.% down of the purchase price and the rehab costsCan be used for primary residence with 1-4 units (could also be looked at as a disadvantage)  When using 2-4 unit property, projected income from other units can be used to qualify 6 months' worth of mortgage payments can be rolled into the renovation budget if the house is deemed uninhabitable by the HUD consultantCredit scores can go down to 600s (lender dependent) DTI can go to as high as automated underwriting system allows (typically 56.9%)Allows you to buy a property in any conditionCan use it to fix minor repairs all the way up to basically a full tear-downFHA 203k Disadvantages: Interest rates tend to be about .25-.5 higher than regular FHA loan Additional costs include HUD consultant fee, inspections, title updates, and supplemental origination fee (Cost of doing business, but this is built this into your numbers, so it's no big deal)Must use a licensed General Contractor for a full 203k or up to 3 specialized contractors on the limited 203k Must hold onto the property for 1 year and live in it. 

(Him and his wife will have a renter's insurance- we are requiring a minimum coverage unto $100,000 but might need to up that if we allow a gas stove).

Florida also has a Windstorm Pool that provides coverage for Wind in certain areas. 

Insurance coverage, creating an LLC?

I'll keep the personal umbrella, and my agent said I can get a commercial umbrella policy to cover the rentals now (at ~$350 a year or something like that), but he also said it might not be necessary, since each property has coverage for $1 million per occurrence and $2 million per year.

If wind or flood damages the interior of your unit, you would have to have those particular coverages to be covered.

I've had some commercial lenders also look at my global debt service coverage ratio, but they don't reduce the income by 25% so my numbers are much better when a commercial underwriter is evaluating me than for a conventional loan.

Even if the property is worth $800,000, the bank will only allow you to cash out in accordance to their maximum LTV  and what their minimum Debt Coverage Ratio (DCR) is.