The best strategize is based on your financial goals and how comfortable you are with renovations and construction.

Unless you’re really comfortable assessing home conditions, don’t take the risk.

My opinion is that it's a math question, I would take the numbers and do the following:#1 Your condo: @what loan amount = cash flow where you are comfortable.#2 Make sure you have 6-9 reserves for the Condo#3 With the loan money, you can explore options with purchasing your primary residence, how much would that help your monthly mortgage instead of renting. ( don't forget about the tax benefits of homeownership in tax write offs of property taxes and interest)I am not sure how much equity you have, but if you still have cash left over, I would consider re-investing in another property. 

Ring floodlight camerasSchlage encode or whatever your local handyman feels comfortable withTowels/bedding-whatever my cleaners recommends in that particular marketStreaming services if available, dvd/blue ray playerHonestly just proper auto messaging through your Management software takes care of most items and makes the guest feel like they are being checked up on.

Will the other room rent cover enough for you to feel comfortable with the deal?

You can make it comfortable and should try to do so. 

(family/friends) I know some people are not comfortable asking those close to you, so it may not be an option for you. 

If you want a job done right, you have to do it yourself" I say you need to get comfortable hiring experts and delegating tasks, or you'll have a job and not an investment.

Living comfortably for very low expenses and enjoying it.

It all comes down to you and what you are comfortable with.