I haven't seen a lot of discussion about this topic which surprises me since I feel like personal finance people talk about HSAs all the time! 

I personally feel it's very intrusive to call someone like this, but maybe it's considered acceptable? 

Do you own these properties in your personal name or through an LLC?

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

JeffWe lead a couple investor meet up groups in person and live stream about the Central Ohio real estate market.

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.

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.

Simplify the structure as much as possible, have clear roles and responsibilities that are not overlapping (meaning only one person is allowed to make certain decisions) and a clearly defined exit plan.

Others may have personal experience to share.

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