As many times as you want to pay the thousands in fees and go through the pain. 

Buying at the peak and watching things get closer to underwater over the coming months of a recession would be painful. 

Quote from @Robert McCormick: Hi Robert,I am not a Broker, but if you are an introvert, pushing yourself to go out of that shelter bubble will be painful, but do-able.Maybe get hypnosis to make you more extroverted and less introverted.Maybe look into attending a live Tony Robbins business event vs personal.Maybe go to Dental School (in San Antonio), it's a good job for an introverted person that pays well.Do other brokers out there think that making 1 sale per month is a realistic achievable goal for a new guy.How long would someone have to be in the business to make 1 sale a month?

Either way, sounds like a pain in the rear end.

We offer 4 different payment methods to our tenants: Online ACH via our PM software (no charge) Deposit @ our bank ($3 charge) Credit Card ($5 + cc fees) Mail ($10 charge)Notice we charge a fee for the less desirable options to encourage the behavior we want:)

Then, in theory you can operate out of and brand your mgt LLC.Yes, having lots of bank accounts can be a pain. 

I'd like overpay on systems at the beginning so that theres not a ton of pain to "make things right" down the road. 

I currently own a portfolio of 6 SFH, of which there is one that I bought a year ago and it's been a pain to deal with.After my rehab it had squatters which took around 5 months to evict, then it had to go another smaller rehab and it's still vacant despite lowering the price to the min I can live with.I do have equity in the deal but with the prepayment penalty on its mortgage it won't be enough and I'll end up with a loss (around 5k) if I sell now, on the other hand I have a loan to pay so it's costing me money each month to hold it.Would you take the loss to get rid of the headache or grind through a couple of years to be able to sell it without a loss?

Find out what pain points they have and see where you can come up with a solution.

So far just looking at Realtor.com, redfin, movoto, and Craigslist(which is a major pain, maybe im not doing it right).