I NEVER let my tenants use their security deposit as a prepaid bank for damages along the way.

You won’t be able to borrow the down payment...as per fha plus no HML would make this 2nd mtg loan.You’ll have substantial closing costs/prepaid taxes and insurance also, more than $15k likely. 

Both the escrow agent and the QI said that if I got the prorated property tax back (in the scenario where I prepaid out of escrow), it would be considered boot, and taxes withheld (3.33% in California).

The underlying bookkeeping work (the actual QB file) belongs to the accountant.This still perplexes me - I paid her for the month of March prepaid - only 8 days of work (gave the dear john email march 8th - so how is that not paying?

Lol.Here's a rough idea of what terms could look like for you (assuming your DSCR is 1.00+)30 year fixed rate, fully amortized, no balloons70LTV Purchase on a SFR in Birmingham, AL (not rural)5.625% Interest Rate (Buy Down available to 4.75%)No Origination Points from LenderNo Buy Down Points (2 max available in this scenario)5 Year Pre-Payment Penalty (add 0.375% if you want a 3 year PPP)Broker Fees are usually 1-3%Underwriting/Attorney fees are usually between $1000-1600Title and Pre-Paids and such vary.On a side note, I have lenders who could also do 80LTV on this for 5.75% at par rate (no points).This is by no means best pricing out there, but it should be ballpark of what could be available to you in the market right now. 

The notice shall be sent by postage prepaid United States mail to each tax notice party and each tax sale party whose interest would be shown on a thirty-year mortgage certificate in the name of the tax debtor and whose interest was filed prior to the filing of the tax sale certificate.

Take advantage of this while it lasts.Lenders will usually allow 2%-3% of the seller to cover your closing costs, pre-paids and other costs(down payment).

Do they apply as "miscellaneous" expense (which I can deduct when I file the taxes of the current year) or add them to the cost basis (which will reduce your taxable capital gain when you sell the house).Here is a concrete example with some made up numbers from closing day:- Purchase Price: $300,000- County taxes from 11/01/2023 to 01/01/2024: $850- HOA Prorations: $30- Appraisal Fee: $400- Prepaid Interest from 11/03/23 to 12/01/23: $1,100- 3 months of homeowners insurance (for escrow account): $150- 4 months of property taxes (for escrow account): $2000- Underwriting Fee: $600- Wire Fee: $15- TITLE & ESCROW CHARGES: ...- Government Charges: ...- 1 year of Homeowners insurance:..- Home warranty: ..How to track all of these?

No bookings for traditional party nights like new years eve, Halloween, graduation, etc....unless it is a prepaid multi-night booking. 

@Cara Lonsdale- Excellent idea about the laundry credit, I'm going to look into the prepaid option which may just work.