I would consider my current situation, in terms of retirement, micro/macro budgeting, and my career income to be in great shape but i'm really looking for new avenues to take to create a passive income stream.

These are just some items in my capex budget, roof 25 year life span, floors 10 year life span, appliances and hot water heater 12 year life, hvac 20 year life span, bath and kitchen remodel 20 year life span,etc. 

Assuming a 4.63% interest rate over 30 years.Here is my budget as best as I can get: Taxes $1,734, repairs $750, Property Management $1375, Insurance $1,271 (this seems kinda high). 

Figure out your budget and then you can see your options.  

Not sure what kind of photo work you do but if it's things like portraits or weddings and those are in the evening or on weekends, that could allow parts of the days that could be put to doing your woodworking.

Given our budget and time constraints (new homes are usually in high tax rates), we only had a couple of options. 

Just know them going in so that you can properly budget.

My thought is gradual updates are easier on the budget than keeping it as is for years and then having a large reno I need to do to get it back on track and should increase rents along the way. 

Identify your criteria, set your budget, and get a preapproval letter from a lender so you're ready to offer immediately when you do find something.  

As I run my numbers I don’t create a formal SOW, but do have a spreadsheet breaking down my budget for what I want/need to fix on the house.