Currently I'm looking for some kind of methodology, software or app, that I can use to manage the properties, which will allow for another family member to step in to my role relatively seamlessly if I were to pass in the future.

This is the best way to get good at analyzing deals and will allow you to quickly have a good idea about how a deal will work.

My advice would be to follow up with Vitaliy and pick his brain as much as he will allow.

I applied for a HELOC and when they ran the title it came up that the 8k grant is actually a second "soft" lien against my property that will go away after 5 years which prevents this bank from allowing me to have a HELOC.

Tangible personal property identified in a cost segregation study is what allows you to accelerate depreciation.

@Matthew McCarty and @Aileen OuyangInvesting in anything is specific to each individual's goals.

Additionally, it feels the most appropriate approach for both profiles I described above and allows me to focus on learning one strategy.

First I follow the law , it allows me 1/3 down .

In my experience, allowing these professionals to guide you can be highly beneficial, as they are likely to recommend properties they would be comfortable managing.

I've been studying for a while and see investing as a cycle, times of high activity (chasing the deal) and times of latency (allowing the deal to mature).