I will say that the wholesale market here is incredibly competitive.

It's very competitive to recruit realtors, you have to train everyone, you have to create your culture, processes, a ton of stuff.

I have zero competition right now 

You could sell and 1031 it into the next property but you'd usually have to time the sale of your existing property and the closing of your new property right.I also wouldn't worry about having central air in the property unless that is essentially a requirement for you to remain competitive with the rest of that market.

If the answer is yes, you can go Nathan's route and maybe recoup a third or so, but IMO not worth it.We focus more on preventing these situations in the first place with solid screening and frequent inspections, once the damage is done it's too late.Milwaukee is currently the second most competitive market for tenants right after Mimai, FL according to the Q1 report from rentcafe.

Claudia, They've recently become more competitive and I do recommend them. 

Would a property management firm even take me, considering I would be their competition once the two years pass?

Many of these platforms also send the same leads to multiple agents.Since most of these paid leads require work/follow-up anyway, have you thought about paying less $ for leads where there is significantly less competition?

It's a higher priced rent but very desired location, updated, and compares favorably to others listed in the area --- and still priced competitively.

It is hard to win with 3.5 down in competitive markets as well right now.