For your current place, what is the cost basis for the property and what would it be worth if sold today? 

Since your last residency was in 2020, you do not meet this requirement, so the exclusion likely won’t apply.You'll need to calculate the capital gains based on the difference between the sale price and your adjusted cost basis (original purchase price plus improvements and less depreciation taken).

I was incorrect.You're good, we're all still learning every day! 

That way we could either claim expenses as deductions or through depreciation, rather than just as an increase in basis for capital gains if it was our primary residence? 

Travel costs being deductible will depend on the purpose for the travel to the area.If you have a rental in the area, then they are deductible rental costs.If you don't have any rentals in the area, they may be explaratory costs and may need to be added to basis.

For example, It may take me 10x as long to do the work of someone who does it every day.

I reviewed Form 8824 and after much research I generally feel comfortable completing the form as well as how to depreciate the carryover basis and additional (or excess) basis using either of the two allowable methods (general and simplified methods).  

Hi @Adam HoekerI have my clients all on QuickBooks Online.We sync in their accounts to reduce human error in entries, and track each property's expenses and transactions to prepare for Tax time, this helps us to be prepared for 1099s as well, track Asset Basis and Depreciation, Mortgage Balances, and any Equity items.Since QBO is very common, it is easy to connect a Tax Accountant to this as well and have them pop in to grab reports they need to file. 

While personally I'm interested in growing my portfolio of mid-term rentals around the Raleigh Triangle market; Professionally I will be connecting with dozens of investors on a daily basis and would love to provide added value by offering access to a wide range of real estate support services.

I don't think this is a good idea for the sole fact that you intend on selling after his passing.Once they pass (which I hope is a long time from now), those who inherit the house will benefit from the step up tax basis, meaning the net proceeds could be TAX FREE.