Prices cannot keep going up forever, they need to at least stabilize to be affordable.

Question 2 - Any suggestions of a good (affordable/free) site that will allow me to set up a late fee each day? 

After they pay 2k for a week they can afford my security deposit knowing they get this back if they take care of my house.

.), and while doing that, save more money and understand what you can afford and what you want to buy.

I live in Buffalo, NY and housing is pretty affordable. 

Because the payments should be interest only, and your being charged simple interest you will end up looking like you have more money available to allow you to afford a higher heloc amount.

i'm certainly not an expert, but i ran thru something kinda similar and i'll tell you what my lender said. so i was living in a home, yet i was purchasing a new home. to afford the new home (which would be my primary after the fact) we had to refinance the current home. we planned on making it a rental. so anyway, our lender required us to live there for at least 30 days after close of the refinance to qualify as owner occupants. this wasn't too big a deal because they were doing the other mortgage as well, so on day 31 we closed for the other property. so i guess my point is, talk with you lender about it, don't lie to them, ask them what are the specifics to qualify. otherwise be careful because you've most likely signed paper or will be signing papers that would make you liable for fraud if you don't walk the line. good luck!

If you can afford to mail every property, go for it, no harm in trying.

This recent article got me thinking a bit more about our market here.https://www.marketwatch.com/story/renting-is-more-affordable-than-buying-in-47-of-these-housing-markets-and-they-tend-to-have-one-thing-in-common-2020-01-10Currently there are 2476 homes for rent in the OKC Metro for less than $1400 per month. 

Also because rents were so low, the property was cheap and I could afford it.