Are you confident that they have processes in place to prevent future mistakes?

If you could help me with that and let me do my research I'd love to use you as  my realtor for my first purchase" I'm sure they will be more than happy to have a future prospect in you.

yes it is unconventional but because of the seller status and the fact that he's selling three at once I really needed to know that I had a buyer in place. the seller would be a great contact for the future and the spire is someone that I've spent a lot of time talking to and seems very genuine.

It's not in too bad shape, but was a smoker's house and hasn't had any cleaning done in years.Based on a quick walk-through I'm looking at internal painting, minimal external painting, carpet replaced (or removed to get to the hardwood floors where possible), a bunch of minor repairs to things like gutters/eaves/etc.In a perfect world, this relationship would continue to care for the property as issues occur in the future.

Someone with expertise should be able to quote a flat rate for the entire project and for each stage of the project.I would expect a lawyer to charge more if getting paid depends on future events, because that means more risk for the lawyer.

The experience i gain will ideally coincide and strengthen my future buy-and-hold rental portfolio.

Not sure what is legal in your jurisdiction, but you could consider using all kinds of things as collateral: life insurance policies, future paychecks, artwork, etc. 

Will it cause problems with future renters or resale? 

A living trust can be a great tool to not only let you dictate the future of your hard earned real estate portfolio while you are still alive but can help reduce estate taxes, ensure a step-up in basis of your properties to eliminate or reduce capital gains and avoid reassessment of your properties when you die so there won’t be a large increase in property taxes.Long story short, please go see an estate planning attorney!

While I can pull in money hand over fist, my concern is that a 90 year old building in such a small area might be hard to get rid of in the future.