I want to invest in area with good clientele, but is concerned that Boston market is already appreciated to a point that I have missed the best time to invest.Any suggestions?

It seems to be a concern of yours.

There are other concerns.

The area is my main concern.

I'm not gonna be making payments  or take any piece of the cake once they sell their condo I just want to help them lower their monthly payments but the same time I'm concern if I will get hit w/ taxes.

I'm concerned that this might slow my investment goals down.

In that environment, most of a passive investor’s concerns related to honesty, transparency, accuracy, and timeliness are managed by the administrator who is a neutral party.

Another concern would be using unqualified help to perform your rehab.

My insurance provider also said I can change the policy to cover STR and put it in the name of the LLC.But I'm concerned that the lender will have issue with the house being used as an STR since we secured the loan as a "second home".Did my mortgage broker lead me astray with the manner in which we secured the mortgage?

In addition to the concern about the 10% early withdrawal penalty, we also have to consider that those dollars from our 401k will now be taxed so they add to our W2 income for the year in which we take the withdrawal.