You'll find me wearing jeans and a $9 black t-shirt from Target and I am not afraid to get my hands dirty, if I can fix something on the spot with what's in my toolbag before I call a contractor.Most tenants think that you are rich anyway, because why else would you own multiple houses?

Even with rents increasing at a rate of 2-3% per annum (in an actively declining rent market today) vs stable mortgage payment above, the later wins.Buying at the peak is never a good idea, even if you went to a Grant Cardone seminar and wear a 10X t shirt at night. 

If you're just starting out, one of the best things you can do is focus on a market that gives you room to make mistakes without losing your shirt—and ideally one that still cash flows well with strong long-term upside.

I agree with the overall sentiment here that the OP should take off his shoes if requested.But may I also suggest that this is a cultural thing, and that to someone who isn't used to such a request that the very request may sound inappropriate and like an intrusion- like being asked to take off your shirt.

You have no experience in STR's, so before you make a huge mistake and buy a property, arbitrage may be a good option to "Get your hands dirty" without losing your shirt. 

They were all wearing FlipSister shirts!

One question for you: Where did you get that t-shirt?

If they can't get three plugs of ice cream and a t-shirt, then what's the point? 

You must balance purchase price, ARV, with renovation costs and still come out on the other side without losing your shirt.

I am in the driveway with the aluminum brake , bending some trim for my house , and a young guy with his company shirt tries to sell me home improvements .