It wouldn't make sense to choose a city where you'd spend significant time and money battling regulations just to conduct normal business operations.

- How much would you suggest spending on a property(s) in my situation?

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

At the same time that made me want to put a ton of work in even more, because I would feel so stupid to have squandered such a rare opportunity.  

I used to spend weekends doing this, and sometimes I'd spot opportunities others missed.Also, have you checked out any local investor meetups?

If you own your washers and dryers you will probably make some decent money but get ready when something breaks and the tenants want it fixed right away.If you are priced lower than the local laundromat (which most are for some reason) your tenants not only have to carry all their stuff to the Laundromat but will have to spend more money and may want you to cover it.Also a Service Tech will probably charge $100 to show up plus parts. 

Know what you are spending $$ on the list. 

I spend an inordinate amount of time trying to fight against the tide of YouTube gurus that encourage brand-new investors to set up an LLC before even buying their first home.

 Wale, thank you very much for you golden nugget I will definitely spend the right of highschool preparing as best as I can for the future!

These areas will require a good amount of on the ground knowledge that you probably don't want to spend the time getting.