The inspection recommends grading the land next to the property and installing a gutter extension to prevent further washout and settling.

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.