Has anyone found an excellent software to manage these transactions.

I'm not sure if there is a creative way to accomplish my goal through that software that is integrated as well.

Taxes, insurance, pest control, utilities, software, etc comes out to around $13k per year each for my 2 bedroom cabins.Also unplanned capital expenses will add up.  

I'm co-owner of a small 2 man software dev shop. 

You've already been on the sidelines soaking it in, now it’s game time.

One of the side benefits is that the tenants now have skin in the game so to speak, and my gas bills have gone down a bit.What kind of heating system do you have in your property?

2) Grace Period: 5 days- Many judges in our area frown upon no grace period- Ours is voidable if tenant is late more than 3 times in a 12-month period3) Late Fee 5% on the 6th- Our software auto-charges- We will waive for a GREAT tenant, 1 maybe 2 times annually, just like a lender may waive the occassional late fee4) Daily Late Fee: 10% per diem- Our software auto-charges- We added this years ago when a smart aleck tenant, upset that we wouldn't waive their late fee, told us they would pay the last day of the month.- Judges often throw these out:(5) Eviction Notice for Nonpayment of Rent: sent ASAP- In Michigan, it's a 7-Day Notice- Our staff bulk sends on the 6th of each month, no exceptions- Even our best tenants get them and we just tell them it's automated and they can ignore if they payRecommend you have a detailed Eviction Procedure and follow it!

It seems like the condo you linked is almost geared towards short term rentals, so you should be in the clear on this specific situation. 2) I would take a look at some STR data either via a dynamic pricing software (pricelabs, wheelhouse, etc.) or take a look at Airdna to take a look to see what is the “sweet spot” is in terms of size of rentals in your market.

Theres lots of books, info and software.

There are always tradeoffs in the game of investing and tax strategy.