3- If its Taxable to them; Must we issue them a 1099 next year for the $30K also paid to them or HOW would you handle that? 

Think there will be a revision years down the road to fix some stuff. 

My Rogers Park small 550 sq ft 2brs were $1250 in 2020 then $1450 last year and this year got $1600 with 3 apps on the last listing.

We have just 5 properties, but with turnover each year, it is very time-consuming to figure out security deposit refunds net of any deductions.

When prices are high, more people are forced to rent, which results in increased demand and rising rents.Inventory has been frustratingly low and is not getting betterSales inventory plummeted at the beginning of the year and has remained below one month in Q2. 6 months is considered a balanced buyer/seller market.

As for cash flow, from sales; probably in year two and three which should match the timing for the housing  market to reset past bottom of market and on to the stable appreciation side again.

NY. 5 year draw, IO for 5 yrs and PI for 10 year repayment period.

I know it's not specific software for mileage or book keeping but I have 4 properties, have been doing this for 3 years, and just made a simple google sheet to track everything. 

Each of them had $20,000 of unused "suspended" losses from prior years plus $5,000 of current year losses.

Jorge here—I’ve been investing in the area for 20+ years.