Would love feedback from anyone with personal investing and/or property management experience in these cities.

Some high-end STR's (like in Joshua Tree) do use professional models, but for your market and property type, I’d suggest removing personal photos and focusing on the space itself, so guests can imagine themselves there, which is really what you want.You also have 81 photos, that’s too many.

While this job could be performed remotely, working with my peers in person for at least a year is important to me.

However, you can get loans that are based on the performance of the rental and not your personal income and debt.

Nice to connect 😎Its in Joliet - Cathedral area I hope to meet you in person as well?

I've walked their properties in-person, and their build quality is good.

I spend roughly $120k on my renovations, but this is for the entire property and developing the secondary suite which certainly costs more (2 new furnaces, all new plumbing, new kitchens and bathrooms with tiled floors and showers).All said and done, I personally love it.

If it's a consultation with him personally - it should be very valuable.

I personally leverage, but have a large rainy day fund. 

I bought this property with a private interest free loan from a friend. the person i bought it from need cash fast so i offered them a low cash offer and they accepted.I had enough money saved up to rehab the house with my savings.