I am just looking for advice on how to handle the situation being a complete amateur.  

Reducing income to avoid operating your business is the amateur approach of potentially saving nickels and dimes and allowing the dollars to escape.

No professional business person would voluntarily devalue their investment when there is no external business pressure to do so.If a landlord is not charging market rent and is not giving annual rent increases to insure their increased expenses are being covered by the tenant then they are not a professional landlord.Call them amateur, hobby or what ever you choose but they are not a professional landlord if they choose to supplement a tenants rent for what ever reason they may choose to justify their decisions. 

I am as close to 'amateur landlord' on the spectrum as is possible.

Here's my two cents from the perspective as a amateur horticulturalist and someone who has landscaped an entire yard from scratch:The price you're being quoted is crazy.

. - Amateur hour, newbies with money burning a hole in the pocket- Experience sponsors with money burning a hole in their pocket- 1031 folks with money burning a hole in their pockets- SpeculatorsA ton of people have done stupid things in the past few years and have been handsomely rewarded.

Lots of deferred maintenance, not major things, but stained asphalt shingles, gutters need replaced, brick building need power washed, a couple of the fascia and soffit boards need replaced, all trim needs painting, ugly amateur ceiling repair where leak occurred, missing drop ceiling tiles in bathroom, no landscaping.

Hand-written letters give the appearance that you are an amateur.

Account ClosedLots of great comments and suggestions have been shared, but if I could add one thing... it would be to treat every aspect of your career as a PROFESSIONAL, not an amateur.A surgeon wouldn't operate on you without knowing how to successfully complete the operation, yet amateur agents try to help people buy or sell a home all the time without having a damn clue as to what they're doing.Professionals learn every aspect of their trade, and never stop learning either.

That's super amateur looking.