If you do things wrong you can lose a lot of money.Your choice is a personal choice which will depend upon your attitude towards risk and your financial ability to handle any surprises.

I retired with the ability to live in an A neighborhood but chose not to spend that much money.

Cash Pros: no mortgage, ability to take it all out in refinance, can leverage (finance) House 2 b/c House 1 is all cashCash cons: the cash is temporarily (or permanently) gone, not leveraging the most out of your dollar, if the property doesn't refinance where you think it should - you can't get all your cash backLoan Pro: potential to maximize your leveraging ability, tax incentives, experience in going through the loan processLoan Cons: holding costs/mortgage payment, acquire debt, interest rates rising make it tough to refinance (for the time being)-----Depending on the amount of capital you have, I might recommend the BRRRR strategy.

Its a long term play as you can have both elements of cash flow and appreciation. 

Yeah, probably a bad analogy and I'm not saying it just to argue, but at some point, competition lowering the prices for renting the nice places has to weigh on the rents (and ability to raise them in the future) of the mom and pop units, right?

Even if the payment goes up it's mostly towards interest (a write-off) and I don't know anyone that doesn't like lowering their income tax.The only other thing I'd ask someone (loan officer) is if doing a cash-out refi would create any large challenges around your debt-to-income ratio and hurt your ability to buy a subsequent property.

We ended settling for 3% on the first deal, 2% on the second deal and no fee after that.3% may seem high but it's a fair cost given that we now have the ability to build a long term relationship with a new investor.  

Hi JasonWhat works for me is find  the big real estate companies who have the ability to buy several deals.

I have the option of using an online brokerage account like fidelity which will have checkbook control and the ability to invest in stocks and mutual funds along with a loan option.

So when my lender said quitting my job would not effect my ability to get a loan I did it.