I would be on the fence as well.

If you go in swinging for the fences, don't be surprised if you strike out. 

New roof, siding, soffit, fascia, flooring upstair, repair fencing, yard work/landscaping, new flooring upstairs, new vanities, kitchen remodel, new paint job What was the outcome?

A low-cost investment in fencing or a gravel driveway could make the land attractive for outdoor storage.Recreational Use: Open the land for recreational activities like ATV riding, horseback riding, or camping.

The house is a simple two bed one bath with a garage and a fenced in backyard.

After digging through listings and getting feedback for needing a garage for all the toys, a fenced yard for the puppy or in a great location next to work. 

I would advise to buy all of them because it will make it alot easier for you to put capex money into exteriors, landscaping, fixing parking lot , fencing , lighting , etc because sometimes the hoa might not be collaborative in my experience.

Completely renovated main level:* Demoed and redid kitchen with new appliances* Refinished floors and reglazed bathroom* Replaced the roofComplete demoed and finished the basement and landscaping* Replaced half bath with full and added 2 bedrooms* Replaced entire plumbing including sewer line* Added second washer dryer* installed stamped concrete patio and walkway plus fence* All new landscapingWhat was the outcome?

It is in an enclosed gate area that can only be opened from inside the fence so I'm leaning away from using it as storage space while I have other guests staying there.

And the new AC unit (seller put in) was stolen right before move in - thieves climbed a 7 foot fence.