Hopefully it'll prevent this lull in work from happening again.

Related point:  If you are using a mortgage it may have clauses in it to prevent or trigger actions if you do a transfer.  

@Bob B. the HOA stated that, since there are only 4 units, they like to keep the fees low in order to prevent unneeded funds from sitting around. 

Not only that, but home ownership here prevents you from being a victim of rising rents.

You will have to remove snow and salt after every snow - a little over-precaution goes a long way in preventing lawsuits.I actually think your repairs/maintenance are probably fine for the long-run, but you might want to up to 15-20% the first year to get that owner's reserve to 10k. 10k does not solve all problems - but it takes a solid bite out of most.

Replaced ceiling in one BR due to leaks and prevent mold.So, you see the pattern of repairs coming every 10-15 years.

This is definitely the biggest hurdle that is preventing me from buying right now.

Any advice on how I can prevent the build up of rain from damageing my house

This would prevent them from getting their mitts on other investment profits you make on other ventures.

Lots of tasks to keep track of, and easy to forget - if you are renovating, think of all you can do to make the house guest friendly, like having the pipes on an INSIDE wall not an outside wall to prevent frozen pipes which can be a nightmare.