I'd start by thinking about which features you prioritize (this could be tenant management, online rent collection, rental accounting, etc.) and then narrow it down from there. 

It may help to prioritize the features you are looking for. 

It's easier to play it safe...but relying on safety limits your opportunities in the future.4) Always ask questions even if you think it may be a "dumb" one.

We (and I assume everywhere) have a local housing inspector with those programs tour the property to make sure it meets basic safety standards (handrails, smoke alarms, etc), and they also reinspect annually, so before you get ready to lease to a Sec 8 tenant, would talk with the local dept. for a list of their most common failed items to make sure it'll pass.You also sign the rental paperwork that Sec 8 uses and know some local landlords didn't love that aspect of being told what lease form to use.

Sale Items:  1) Condo sales are the most difficult(or should we say the most annoying) , right up there with multi family sales, because VT requires the seller to do a Fire and Safety inspection at the time of sale (this is on top of the buyer's home inspection should they choose to do one-- which most buyers do).

My eventual goal is to create enough passive income to have the opportunity of pursuing investing full time, or even added safety for pursuing self employment of any sort.Looking forward to getting to know the community, and of course getting started!

My opinion only: books are a waste of real estate investors time & money. 5) Other suggestions: ask your insurance agent to walk the property with you to look for safety issues.

The railing may be a safety issue or a non-issue, depending on local code because it’s only 2 steps. 

It is surprising how many BP posts are about very basic info- local LL/Tenant laws and Real Estate licensing laws; IRS rules; Fair Credit Reporting laws (that affect anyone that is approving/denying rental applications); EPA rules regarding lead paint, asbestos, waste handling, runoff, and more; Worker's Compensation (insurance) laws; OSHA safety rules; contract law basics; Accounting best practices; HOA rules, budgeting, and reserves; Building codes/permitting rules; and plenty of local ordinances.

Additionally, there are certain laws and regulations that you must comply with when renting out a property, such as obtaining a rental license and meeting fire safety and other safety standards.