If you need any help with trying to bring a certain level of automation to your rental process (ie. now that you have a lease signed and he's paid the deposit, you can make things easier by collecting rent online and automate some of that maintenance request process); additionally, there are definitely tools out there to make managing all 5 rentals super easy.

If he's worried about the rental management process, tell him there are definitely some tools out there that can even help you to automate the rental management process. 

Hey BP,I work full time in the tech industry mostly revolving around server administration, but with a specialty in simple automation.

@Jeffrey Allenczy  Really get your processes down and make sure you stay on top of local events that drive up prices (or use something like Wheelhouse to automate that for you.) 

Is there a way to automate the switchover?

Although I originally looked at it as an investment, I would buy this particular home as an owner/occupant and move into it after reno.I have spent a whole month teaching my agent everything that I’ve spent months researching about how to bid on HUD homes, but she has little kids and a couple of times has gone to bed with her ringer off and I can’t reach her when I see the house is back on the site and need her to put in another bid.I am fed up.I have read on this site that some people have NAID numbers and automate their bids. 

Once you do decide to procure your first rental, definitely lean on the BiggerPockets community as a resource; I'll also say that it could be worth considering a shot at a software solution built for DIY landlords (1 - 15 units) to bring some automation to the rental management process (just to make things much much easier for you)!

Hi Chad, it could be worth considering a shot at a software solution built for DIY landlords (1 - 15 units) to bring some automation to the rental management process (just to make things much much easier for you).

We use Dropbox for secure storage as a simple "owner portal", and we integrate HelloSign with it to automate lease signing at a distance.

What technology solutions do you recommend for automating new and current customers?