@Tom Ott  the old rust belt cities have such huge swaths of demographic shifts with erosions of values to the point the homes cost 1/4 of what they would cost to rebuild .. these areas have turned into the land of the turn key operator or landlord rental area.. and as such the values are more commercial in nature IE they will never really move unless rents move... as long as rents are stable ( which in my 20 years of working in those markets they have)  Investors just back into what they will pay for a given cash flow.. the property is just a vessel if you will.. since there are more homes than butts to put into them in many of these areas.. like Detroit you could bull doze 30k homes and still have left over housing for the population.Down town resurgence is happening in virtually every big city as the millinial buyer and older folks as well are tired of commuting and want a different life style.. and developers are filling that niche.I know in Portlandia its very true. 

Yes, you must capitalize the cost of the improvements due to enhanced repair regulations.

Consider doing a flip or two to enhance your cash pool then buy at a low LTV for cash if needed.Be careful of those who claim to be private lenders online.

And you like your job, which is great.So work your job/freelance, live a reasonable but fun lifestyle while earning more than you spend (seems common sense but very important) and then invest the difference in turnkeys.

But start with your affinity groups; most of the major listing sites have restrictions on listing rooms for rent -- just a fyi. and lean on local connections based on your lifestyle/standards.

It could also be buying a 2+ bedroom house and renting the other rooms out, if you’re open to that kind of lifestyle.

It also keeps us from feeling rich and spending frivolously on lifestyle. 

That will eventually allow me to quit my W2 job and focus on real estate but still maintain the life style we want and remain bankable.

Even as a resident, I never considered condos because of the high condo fees and communal lifestyle you are forced into.

Thanks @Morry Eghbal San Diego is my target, on the top 3 places for lifestyle and real estate.