I recommend doing a flip when you do not have any money.

For those who have more experience investing - what would you recommend I do here? 

STR management is 20-25% (I would recommend self managing or getting a VA), since income is higher you could probably get away with 5% for maintenance / cap ex but remember you need to cover utilities and cleaning for these units which drives up costs.

Professional guidance can be obtained from local personal experts experienced in your particular niche.  

I want to use the profits from flipping in my home market to obtain and pay off properties in a better cash flowing, landlord friendly market.

I highly recommend an ACH service.

Most of what I’ve read you obtain the code violation list from a city official but it sounds more like you are purchasing the list from an external source? 

I also liked that they are US based as I had issues with my bank with the Finland based Hostaway.Finally, I highly recommend PriceLabs.

It's a balance of cashflow and wealth accumulation.One of the goals is to have tenants pay as much of your cost-of-ownership as possible (loans, taxes, insurance, etc.)In high-cost areas, any Class A or B property you buy will usually negative cashflow for the first 3-5 years, until rents rise enough to cover the negative cashflow + rising taxes & insurance.Investing OOS increases your risks because you may not know the market and you can't check on everything/everyone all the time.If you move forward with your buddies, HIGHLY recommend creating a solid Partnership Agreement!

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end?