So if I’m in my mid fifties and want to retire within seven years. Are buy and hold rental properties a bad idea at this stage?Even with fifteen year financing and with some cash flow from day one, equity payoff, appr...

Due to his age, I want to help but not to his detriment.Please advise!

Renovating the amenities, property exterior or units and increasing rents.Syndicators conduct a market research and analyze nearby buildings with similar vintage (age), amenities and renovation level.

Get the funds needed from a syndication, hire out every job, exit in 3 years and get your F.I.R.E. by age 18. 

If they are VERY professional, they will have their processes in writing as verification that it is enforced equally and fairly by their entire staff.6.

(We are a blended family with 8 kids ages 19-26)  They have all worked for us in our construction business and the short term furnished rentals. 

Typically, do people who retire early just pay the penalty, is there a way around this, or are they using taxable accounts until they reach the typical retirement age?

Maybe Murphy's Oil soap all of the wood and leave it as is and see if it rents.I say that because you don't know what's behind that paneling (cost $$$)(40 layers of wallpaper, giant cracks in the lath and plaster, etc...) and from the pic it looks like a lot of cabinets (cost $$$) to replace.If it were mine and I decided to leave it as is, I'd probably do the kitchen floor in (period type) 12 x 12 squares and replace the carpet with dark LVP and see how much rent I could get for it.Probably a new Formica top and a new Dish Washer (just to avoid service calls on the old one) and Greige the wall color.Of course from the pics I can't tell the condition of the cabinets--but have have seen similar ones of that age in incredible shape.Good Luck!

In a city like Chicago with some age, the inventory of 1960s and later buildings are tougher in the city.  

However, Google, especially for Google My Business, is now insisting that photos of the store front with a legitimate business sign be provided for verification.