I'm a big fan of the house hack. 

Personally, I'm not a huge fan of Boston and Brookline investing and am also not too keen on condo investing unless you are on the Board. 

Being that the property has been listed for so long and there are a few major issues, I am thinking of putting in a lowball cash offer (I am not a fan of lowballing, but I think this could be a win win). 

I'm not a fan of CoC as it can "allow debt to make the deal". 

Its a virus not unlike Covid right now in our industry with advance scheme fake lenders taking advantage of those that dont understand how HML works.If your an American Greed fan  find the episode on Remington Financial and INgrid Robinson.. its an eye opener. or just google Ingrid and advance fee schemes she has a website dedicated to it.. 

Actually, I'm a fan of offering people more time then they asked for.

I would look into Hermosa, only issue is no train to get to downtown quickly ( have to take a bus to the blue line).Big fan of the areas your looking into.

I am a big fan of personal development.

They will know who to approach (that will be more newb friendly) and they will end up getting you the same rates as if you had experience. 2) Lender/investor with deep pockets: this will give the banks confidence that if **** hits the fan you'll be able to cover cost over-runs.

@Osvaldo Benavides, I am a fan of GC, but it depends on your budget, knowledge and ability to oversee the project.