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.

I highly recommend an ACH service.

I recommend having an attorney draft one that can be short.

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.

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

Buyer's agency agreements were already required here before, our regulatory agency just went from strongly recommending them be signed right away but not really requiring them until writing a contract to 100% requiring them to be signed prior to showings.

Pricing has changed but J Scott's one of the smartest guys around and is one of the books I always feel comfortable recommending.

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!

making $150 net in month 1 because a spreadsheet said so is fantasy.here's a fantastic thread about 'cash flow' investing from California - i highly recommend it.https://www.biggerpockets.com/forums/48/topics/1159104-overl...i say all this not to be discouraging but to be realistic - hope it helps