I forget; it was payment processing related) that required me to have a website for the business.

Risks include market fluctuations, property damage, tenant issues, and unexpected expenses.

@Ryan BroschardHi Ryan,You have hit a common issue many new investors fail to anticipate.  

Another nice bonus of using this as a funding source is no closing costs, big help on the front end.Obviously, if all goes relatively well, the plan would be to hold these properties as rentals and refi at some point down the road when rates on mortgages drops back down a bit, whenever that may be.

@Rachel Jane a lot of issues here to consider:1) Does the condo association even allow rentals?

I even try to unsell them on the business by sharing my financial losses, litigation,  market shifts, permit purgatory, shady contractors,  clouded title issues,  paranormal activity, squatters, mold, etc.

I bet if converted BACK, it would be 4br+, probably a rather spacious 4br+: - a whole lot easier to rent given much more demand for such vs efficiency or 1brs- no longer competing in any way against apartments- no more utility issues, because tenants cover 100% of there own utilaties- no more headaches of wrangling different persons to play nice togetherAnd on and on and on...... 

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.

They might only skim an inspection report and trust me to find issues.

Private funding from a relative may provide flexible terms and reduced financial risk, but formal agreements are necessary, and interest paid is deductible for you but taxable for them.Traditional investment property loans offer stability and tax benefits like deductible interest and property taxes but require larger down payments.