On the other hand, I feel one of the main advantages of passive investments (via syndication/crowdfunding) is that I can hire a manager who has years more experience than I can ever hope to obtain myself.

Offer the main house as a STR (we would stay in other parts of the property at times if needed). 

Some of the main reasons I started this journey is so I can eventually take my family on trips to experience different cultures, help less fortunate people, and build generational wealth. 

Also, lets say Khadijah gets a contract to purchase 123 Main St for $50K.

Mainly those that have seen sharp price increases without incomes keeping up.

Let’s say the main tenant accounts for most of the annual revenue with a lease ending soon (is healthy and probably looking to resign).

I'm needing to take over management of my rental, and I'm wondering how those of you who manage remotely handle packages, for example, for supplies, equipment, etc. 

It might make more sense to hire someone full-time on the ground to manage the day-to-day.For tools/systems I think you're going to be looking at the main property management software providers.

To land another FhA without refinancing, the 100mi distance is going to be the main requirement OR underwriters want to see a major life change (having kids so you need a bigger unit is the most common scenario).

A DSCR product is what you are looking for.DSCR simply doesn't take into account your personal income, instead we qualify the loan on the properties rental income (or projected rental income).Your credit, properties cashflow, loan to value & prepayment penalty are going to be the main determinants on what this loan looks like for you.