We self-manage our five-unit property with both—while RentRedi's reports can be clunky, Stessa offers much better reporting.

Sorry to hear your self managing isn't going as planned...finding good tenants is tricky!

Once you're ready for the next purchase, you will have experience, systems, and the confidence to tackle a bigger project like a BRRRR.

When it seems like they have a final bid and no one is willing to increase it, they will often times go talk to the owner for a few minutes.

Converted an empty room to a standard room to make it a 6-bedroom instead of the original bedrooms which increased the rent from $2,200 to $2,800 for Section 8 voucher holders for this zipcode.

Quote from @Cameron Moore: Exactly. 15 years ago, I noticed an increase in owners using insurance to pay for a replacement roof, usually to sweeten the pot during a sale.

Financing seems to be tricky with IRA hence feel that its best to buy with self funding fully.

Some reasons you'd need to sub your tax returns: if you have a schedule C (self employemnt) or a schedule E (rental income). 

You could have your insurance cancelled but more likely you're going to see a rate increase.

It sounds like a single family house where you will be living in the house(personal use).Therefore, you may not be getting the tax benefits you think you are.Consult an accountant.I am not sure why your sister would agree to this as well, she is losing $170,000 in this transaction and she faces the possibility of you increasing her rent.You also have to charge market rent or close to market rent or it is all deemed personal use.