Refinished the original floors (massive value increase), fixed the heating and air system, painted all rooms, cleaned up the yard for curb appeal What was the outcome?

Vacancy won't be an issue in this area and pretty confident it will be filled up as it's near to almost everything like train stations, grocery stores, hospitals etc. 

I self-manage and I just give my accountant for tax forms and total for whatever I spend in appliances or anything else.I need to upgrade my Quicken 2014 Home and Business.

Always increase the rent by something every lease renewal.

If the activity is considred active, then there is an opportunity to increase the loss through the purchase of a cost segregation study which would increase the depreciation into the earlier years.

Thought about adding a smart lock to the garage and making it a self-rental service.

It often results in increased rents for the area. 

Flipping is a self-employed job with high risk and high transaction costs.By the time taxes and agents are done with you, the juice is rarely worth the squeeze.   

Determining whether the venture falls under a service or rental business hinges on the provision of substantial services; for instance, if a bed and breakfast service is offered, it must be reported on Schedule C, triggering a 15.3% self-employment tax.Moreover, personal use plays a crucial role in the classification of the property.

If you are not confident in your own abilities, why not get a new CPA?