I'd say purchase now using the fundamentals - under market price, in need of cosmetic rehab or having some other type of problem you can fix that drives other off.

Now...if only we could convince @Steve Vaughan to come join the dark side of developing hahahaDeveloping would most definitely disturb Steve's daily Napping Routine..    

It came up through the MLS, and although needed some obvious cosmetic work and updates, appeared to be nearly livable with the exception of a single roof leak coming from a unsealed gas line entering above the dryer in the kitchen.

Cabinet demo is one of the most wasteful cosmetic flip costs in your budget and are often scraped for literally no reason aside from the fact that they look like 1997 and the flipper has no imagination. :)

@Daniel Barbosa I assume you are looking for investments that routinely cash flow $500 to $1,000 per month each and not collectively, right?   

I initially wanted to house hack a multifamily property on an FHA loan for my first deal, but I came across a duplex that has one half already renovated and the other half with lots of cosmetic issues.

-ShawnServices Provided:Market and show vacant properties Negotiate and facilitate new lease agreementsEnsure vacancies are move in readyConduct inspectionsInitiate new tenant move in transitionCollect rentHandle customer service inquiries24/7/365 emergency maintenance calls and dispatching Receive and handle routine maintenance requestsResearch market data for appropriate market rent increases and renewalsHandle tenant disputesConduct move out inspections Reconcile and refund security deposits Monthly and year-end owner accounting File IRS form 1099’s on owner behalf Handle any accounts payable (utilities, taxes, insurance, etc) Coordinate capital improvement projectsFull unit turnover coordinatingTenant evictions Coordinate lawn care and snow removal Connect and disconnect tenant utilities Facilitate City of GF Certificate of Occupancy inspections Enforce late fees and tenant maintenance chargesFee Schedule:10% of gross monthly receipts.

My plan is to do my own renovation on the third floor apartment while I live in it, and then move into the lower apartment and do some needed updates/renovations to the bathrooms and kitchens while I reside there. ( all function fine but just need cosmetic updating).

If this is a routine process, it could be a game changer with some of the projections I'm running. 

If I do more of a cosmetic rehab and use a normal loan, will that lender allow the loan to be repaid sooner than 6-12 months if that deal makes sense to flip right after rehab?