I know I could hire a manager acquisitions, but do not have that volume to justify one I think.

You can make a new lease with that tenant proposing a rent raise anywhere from $300-500 but you have to be able to justify it (maybe the property doesn't have central AC, maybe you're planning to do some other type of updating but that can be hard when they're physically living there still if its a bathroom or kitchen) and I would also make it so that that rent increase would go up after 60 days of them signing and agreeing to that new lease. 

The additional income from STR could justify the renovation costs, but it requires active management and market awareness.LTR or Break-Even Strategy: Renting long-term might simplify things, but if it only breaks even, you’re right to consider if appreciation is enough motivation to hold.DIY Basement: DIYing the basement could increase STR appeal without the full $50K outlay, especially if extra space attracts more bookings.

Best case scenario if you get into a gunfight is you are able to shoot first and not get shot, but the result of that will still be awful as the legal ramifications of shooting someone are not something anyone wants to deal with, even if it is completely justified your life will suck for a while afterward.

Part of that you can justify because of the necessary repairs, but overall higher price points appreciate differently.The median home price has basically doubled in Milwaukee from about 160k to 320k in the last 10 years.

Fast forward to today and one of those existing STR's has become a nuisance to the neighborhood and so the HOA board is planning to ban all STR's using what they believe are provisions in the CC&Rs to justify it and have consulted an attorney to validate the legal standing on implementing this ban.The CC&Rs were written in 1998 (before STR's was even a thing) and have these sections being cited by a couple members of the board as justification for banning the rentals (note there is not anything explicit about STR's in the documents)Section 1 – Single Family Residential – states in part, “… Lots… shall be used for no purpose other than residential purposes.”

You'll have to decide if this is a big enough issue to justify finding a new PM.As an aside, you may find a contractor that can do work cheaper, but will they be as responsive?

I added value to the deal by retaining the 3 long-term tenants on the upper level, providing immediate cash flow, while planning upgrades to their units to justify future rent increases.

I added value to the deal by retaining the 3 long-term tenants on the upper level, providing immediate cash flow, while planning upgrades to their units to justify future rent increases.

I added value to the deal by retaining the 3 long-term tenants on the upper level, providing immediate cash flow, while planning upgrades to their units to justify future rent increases.