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

For example, I mention that every adult must pay a $30 application fee, pass my credit/criminal background, make a combined income of 3x the rent, and whether or not the property accepts pets.

I am guessing the beach houses were usually purchased and rented with a goal of “free” family vacations being paid for (along with mortgages) by rental income.  

As expenses fluctuate (property taxes, insurance, maintenance items, etc), the cash flow will be up and down and unreliable.

Evaluating deals on this site will help you understand expenses, income, and financial statement.

Aloha @Daniel Kam - most of Kakaako has a 180 day rental minimum, so if you haven't checked with your building association, I recommend you verify what the minimum rental period is for your building.If you are allowed to rent for less than 180 days, you will then need to apply for a GET license, and well as TAT/OTAT and pay the appropriate taxes on a regular basis.  

Not going to kill it on the rental income, but if you sell it subject to, there is a lot of equity.

Not only will you lose your property tax exemption, but you may need to secure LTR tenants.

It sounds like you understand that you can only 1031 the real estate and will have to pay tax on the portion allocated to the business FFE. 

Examples:44109 (median home price went from roughly 50k to 125k in 8 years)https://www.zillow.com/home-values/77009/cleveland-oh-44109/ 44102 (median home price went from roughly 30k to 120k in 8 years)https://www.zillow.com/home-values/77002/cleveland-oh-44102/ 44106 (median home price went from roughly 100k to 200k in 8 years)https://www.zillow.com/home-values/77006/cleveland-oh-44106/ It has the highest rents on average in all of Ohio for major cities and the median income is not even in the top 3.