I flipped a property several years ago and ended up dumping my gains into an upgraded primary residence.

Prices and rents continue to increase steadily.Sales - $/SqFt by Month(Click to enlarge.)The median sales $/SF was up 9% YoY and 6.7% YTD.Rentals - $/SqFt by MonthRents rose 4.3% YoY and 6% YTD.The Market Remains HotFollowing the rapid inventory decline starting in Q1, the number of days on the market for sales remained below 17 and for rentals below 19, indicating strong demand for both.Sales - List to Contract Days by MonthRentals - List to Contract Days by MonthRental trends tend to follow sales.

We've found it has superior reporting features, integration features, and is overall more efficient to work within than other REI-specific software.The downside is QBO is not set up for REI so you'll need to do that or work with an expert to ensure it is set up for your business appropriately.Something else to keep in mind is your entity structure and how your entities file tax returns.

I ended up moving forward like Matt had said.

Like who will manage the building, what is the collective rent, what are the taxes and insurance, is it all up to codes of the town, zoning questions, what is the as-is value - this will be very, very hard to comp and the lender will come in at the low end of the comps for sure. 

We did set up a separate LLC and purchased and manage our properties finances through it.  

The forums can be a great place to meet folks in similar boats to you, I'd also recommend checking to see if there's any in-person meet ups for your area as that can be a wonderful way to connect with others local to your region.

I grew up in a major football town, and a close family friend rents his personal home out for $3K a weekend. 

When sewer backed up into our condo, association was responsible for maintaining it and so they paid for cleanup and repair/replace of damage it caused to our unit.

I'd recommend reading up on the process more before you start (and local tax sales are coming up soon).