I am sure there are other good choices out there, but strongly recommend them.Stessa is lacking tenant communications and maintenance tracking, but overall stands up pretty well as free, or nearly free.Buildium is pricey and has a learning curve, but if you are going to exceed 20 units, definitely look to migrating to a real professional package like buildium

I hear you, I think the price of turn key STRs are almost impossible to make money on in the traditional markets. 

But for an OOS investor one consideration is access to support, first of all PM & contractors, and you have more choices in the much larger Milwaukee metro area than in a smaller submarket.

Options like our partner Baeslane’s free online rent collection platforms, payment apps, and ACH transfers are convenient for both parties, but traditional methods like checks or cash are still widely used.I’d love to hear about your experiences:What rent collection method do you prefer and why?

You’ve made a great choice diving into real estate investing—it can truly be life-changing.

If it needs that much work will a traditional lender finance it and are you qualified to get financing?

Quote from @Chris Seveney: @Francisco AvancenaThere are specific lenders who will do land dealsBut of course not as many as traditional real estate.The key will be skin in the game - typically for land because it is less liquid than a home the lender will want to have a lower ltv on the deal I fund land flippers currently in  CO FLA WA ID MT NV AZ OR TX SC GA VA  one thing about land though LTV is lower and RATES are NOT the same as typical HML rates are higher for raw land but its a specialty niche and a business that I grew up in..

You can do a duplex though, which might not be a bad idea.With your credit score, conventional might be a good choice, you only need 5% down for 2-4 units if you live in one. 

Maximizing cashflow becomes a strategy choice that accounts for your market and tenants.

You lock in your interest rate and if rates drop you can prepay at any time and refinance at a lower rate without penalty.If the deal is commercial, whether commercial multifamily (5+ units), office, industrial, self storage, hotel, you name it...the choice becomes far more difficult.