With $27000 reno cost and an added $225/mo how long is that to break even?

Adding additional bathrooms (like a master ensuite) can be a game-changer.3.

Bridge Loan with Refinancing Exit: A bridge loan could provide a short-term solution to pull the cash you need now, especially if you’ve already added value through your rehab.

I 100% endorse adding in the escrows for taxes and insurance to set the buyer/borrower up for success. 

I suspect it will be well used and have high maintenance costs.Software: office of google office, asana, possibly quickbooks (i would normally not suggest for a single rental, but the rent by room compounds things).  

@Sean GammonsConsider adding a partner for the second deal to share the down payment and mortgage responsibility, keeping DTI manageable.

Once the property is in service your rehab costs will be added to your cost basis. 

Then I consider letters of reference, cosigners, and added security deposit in order to meet approval. 

Tom, Based on what you've provided, if the property was held over one year, you'd be subject to the long term capital gains rates and any depreciation that you took on the property in the past would have to be "recaptured" (Added to your income) at the short term tax rates (but it will not exceed 25%). 

Since then, I’ve added six duplexes and three single-family homes.Apart from the house hack, if I could start over, I’d focus more on single-family homes in better neighborhoods.