I dont want to think for you or tell you what to do. However, when I was similar sized years ago, I kept all my mowers and fert equipment in enclosed trailers in store n lock parking spots. The guys would report, take their truck/trailer and do their route. Come back, park, and repeat. Just recently, because of how many spaces I was renting, it was actually more affordable to lease a commercial facility.
Advise: dont do anything that the numbers do not justify! Dont build a barn because you WANT it. I wanted a barn for years (as I was doing maintenance all times of the year exposed to the elements). Now that the numbers justify the expense, I have what I want. I have a semi and a half of fert in my building, all my winter equipment is inside, and best of all - so is my skidsteer and forklift.
If this post seems mean, it's probably because I'm drunk posting. Maybe my next one will be better...