One issue I'm running into is my confidence in underwriting all the expenses, and using my HELOC for the down payment.

It could be worth transitioning to a midterm rental if there's demand for that type of housing in your area, like traveling professionals or remote workers.

It was a tough moment, but it pushed me to focus on preparation and delivering my message with confidence. 

Not sure her “design” fee or what was spent on travel. 

Thanks for the vote of confidence @Tyler Carter! 

Giving them a laundry list of items will typically just overwhelm them and create more confusion instead of giving them a smaller step process to get more confidence to get the ball rolling and then they can get into the weeds on their state when they get the contractors out there, have local bids come in, and dial in their plan. 

In rare instances we will let someone pay through Square or Stripe, with them paying the cc fee, but only in unusual cases, such as one time with a tenant who was traveling and didn't have a bank account to use with our online platform.

I've been interested in real estate investment since college but I've either been without the capital or without the confidence to take the first step.

I’m self managing myself but the tax side of it is a little confusing to me but I’m recording everything involved as far as maintenance, traveling, expenses etc. just want to know what some people would do in my situation or what to I can benefit from come tax season  @Angelo LlamasI recommend that you find a real estate accountant to help you understand and prepare your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

Traveled around.