I am still very active in my local market as a host of the WWL Home Improvement each weekend.

We've lived in over 10 homes while raising our 3 children that we improved and sold.

I am optimistic that things might improve with this change, but I would not pay again just to find out.

Clarity shows commitment and improves your chances of obtaining funding, whichever property you choose.

If interest rates settle down and rents improve I may try the Long term route.   

You're also going to need survey and engineering work to get the permits done for putting in the utilities to the buildings, flatwork and other improvement requirements around the buildings.

@Paul Bogard going to assume you are buying this proeprty to live in while you "house hack".First, you should understand +95% of real estate agents ONLY know how to sell owner-occupied properties and are almost useless for investors:(Find an agent that has rental properties themself or can PROVE they've got successful repeat investor clients.Secondly, you can greatly improve your cashflow by renting out your other bedrooms.

Does it improve the roof itself, or does it bring increased maintenance.

Building a Phase 1-5 messaging campaign is the easy part.I'd recommend you build this yourself, so you can see what's working and what's not, and improve it over time with added features, automations, and complexity.

Although I am outside of my comfort zone and feel like an absolute tool (I'm lost and that's uncomfortable), my faith, drive, and want to achieve my family and life goals continues to motivate me to get outside of my comfort zone and push for continuous improvement.