They rare a terrible lender.

I don't think that's what I want to get into, I mostly want to get the benefits of having rental properties that I can receive rental income off of.Once I get enough of a downpayment, I think I should be able to get a loan, my back-end DTI isn't terrible as the only thing that I'm paying for is the car payment of $400/month and we are making about 5250/month gross.

This is referred to as "AirBnB arbitrage" and I think it's a terrible idea.

I truly believe you can find a terrible deal in Dallas and an amazing deal in San Mateo.

I've seen many deals I have done (and others) where if I, or they did rely on a percentage for analysis or projections, made a yes/no decision based on it, and either lost a great deal or walked into a terrible one.Can't do that when you use dollars, when the dollars are based on actual numbers from the market the specific property is in. 

Back in the day, I had a terrible time as a loan broker trying to close a loan with the likes of Wells and B of A -- they are just too big to care sometimes.

If I have run my numbers correctly I think I could rent it for around $3000 and have a cash flow of about $1000 after mortgage, tax and insurance.Big risk = big reward or is this a terrible idea?

Also, and I hope the day never comes for you, but chances are if you are in this biz long enough you will place a bad/terrible tenant. 

Question two: We've had people tell us that now is a terrible time to buy and that prices are really high.

Good perspective, I would definitely look at each building on a case by case basis since they are not all created equal and some of them I think are absolutely terrible "investments" like the condotels (If you can even call them that) and they would be hard to live in full time.