i say that not to discourage you, but so that you have a realistic picture of what to expect.as @Travis Timmons alluded to, you need to be in a strong financial position to even think about starting to invest. 

However, financial freedom isn’t a one-time event; it’s about sustaining your desired lifestyle for the rest of your life.Once you clarify your goals, the next decision is where to invest.Investment Market/CityThe most important investment decision you will make is where to invest.

I have a renter in there now and am wondering if a cost-seg makes sense to do financially as I am planning to keep the place for 10+ years. 

Also, the whole point of hiring a PM is to handle tenant, maintenance, and rent collection, so if your partner isn’t actively managing but just supervising the PM, IMO not worth having a two people essentially looking over the same tasks.Contributing financially for one person and the other having no financial stake raises decision making questions, such as when to sell, how profits will be distributed, etc.

It's mostly Class A properties, a few Class B.You may find the below copy & paste info useful in addressing your question:----------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Unlike banks, which offer limited loan options, brokers have access to a wide network of lenders, including niche and non-traditional financing sources.Here’s what they do:Assess your financial situation to determine your borrowing power.Compare multiple loan products to find the most favorable terms.Negotiate rates and terms with lenders on your behalf.Guide you through the application process, ensuring you meet all requirements.Example: Suppose you have a lower credit score or unconventional income sources.

I would like a payoff planner that helps me navigate the various maturity dates and interest rates of my (15 due in 5) mortgages so that I gain the best financial advantage when paying down principal balances. 

A hard money or institutional lender my be anywhere from 65%-100% LTV.

In order to encourage tenants to get renter's insurance, we have been contemplating instituting a $50 monthly fee until they provide proof of renter's insurance with the owner listed as an additional insured, but not sure how well that would hold up if we ever had to evict. 

Don't limit your future financial freedom to just where you live today.