Saving $10k or $20k off a purchase price is maybe $120/mo difference in payment.

We plan to use short term rentals to cover the mortgage/monthly payments but with the skyrocketing property taxes in that area, I'm concerned we may not be able to net enough. 

Collect a security deposit when the lease is signed and require payment of the first month's rent at move-in.

Figure out what your monthly PI payment can be and go for those terms.     

I have a VA loan option from when I was in the military I have not used and have the down payment I’d need for our next residence so I don’t necessarily need to sell in order to buy my next house.

Payment insurance, underwriting, and third-party fees at execution.

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I've never done a dscr loan but if rates drop after your (most likely) pre-payment penalty ends, I'd refi.

May plan is to pay cash and wait until interest rate improves, then refinance and pull out $150k for a down payment on a second property. 

Obviously there will be other items that come up but it's a good outline to start.AddressPurchase PriceDown Payment (20% if HM)Loan AmountRehab Cost Est Interest Rate# Holding Months Homeowner's Insurance PolicyOrigination FeeDocument FeeHOA Fee if applicableProperty TaxesTitle - Lender Title InsuranceTitle - Owner's Title InsuranceTitle - Binder Fee - Buy SideTitle - Binder Fee - Sell SideTitle Messenger FeesRecording Grant Deed - Buy SideRecording Trust Deed - Buy SideRecording Fee - Sell SideStatement Fee - Sell SideEscrow Fee - Buy SideEscrow Fee - Sell SideSub Escrow Fee - Buy SideSub Escrow Fee - Sell SideLoan Doc Signing ServiceMonthly Int Only PaymentNHD Report $99Utilities (Electric, water etc)Owner's Title InsuranceTransfer Tax - Sell SideHOA Docs Order if applicableHome Warranty $500Agent Commissions (4-5% of sale price)Wire Fee $25 per wireFiled Articles of Incorp for LLC (if creating a new LLC)ARV #Minus Down Payment Back (20% if HM)Minus Rehab CostMinus Holding Costs, HM FeesMinus Realtor Commissions (4-5%)Net Profit