OR Should I buy 4-5 single family homes instead?

Those Annuities don't sound great, 6.4% yield if just you on the policy and only 5.8% if you add your wife to inherit the policy if you die someday (sorry but high likelihood, nothing lasts forever)consider as recc above, find a few good syndicators with several upcoming deals you can identify within 45 days of the sale of your condos (sell all 15 as a package to some investor), then invest as a TIC, tenant in common, with one syndication deal, there won't be any fees, then make sure it's a longer term 10 year at least investment, then keep rolling until death.

It’s 30 days, however we usually provide 45 because 30 days can be tight for them then to figure it all out.

I do think I probably had to pay 4-5 points though.  

.% of Original List Price Received: Sellers received 94% of their original list prices, down from last year's 96%, indicating minor shifts in negotiating power.Median Time to Contract: A significant change here, with the median time to contract increasing by 73.1%, from 26 days to 45 days.

We manage about 10+ MTRs in Indianapolis, but we have less than 45 days vacant on most units!

(and I have full time job so time is limited)Here’s a breakdown of my investment plan–I would greatly appreciate any guidance and recommendations on making this (or some version of this) happen.PropertyLocationAttributesB-level areas (A-D scale)Safe enough for my girlfriend to feel generally safe walking alone in the eveningWalkable neighborhood / close to transit (car ownership not necessary to live there)Area(s) of interest (not set in stone)Jersey City areaConditionB or C-level (A-D scale)Semi-distressed with potential for minor rehab upgrades ($35k max)DealbreakersFoundational issues / big required rehab due to FHA 203(k) max for streamlined versionSize2-4 units (higher the better)2-4br per unit preferredMax Budget (FHA loan limits)NYCSingle-Family Home: Up to $1,089,300 + 3.5%Duplex: Up to $1,394,775 + 3.5%Triplex: Up to $1,685,850 + 3.5%Quadplex: Up to $2,095,200 + 3.5%Hudson County, NJSingle-Family Home: Up to $1,149,825 + 3.5%Duplex: Up to $1,472,250 + 3.5%Triplex: Up to $1,779,525 + 3.5%Quadplex: Up to $2,211,600 + 3.5%TimelineTitle in-hand latest: Jan-Feb 2025Can potentially buy earlier if I sublet my current apartment in NYC as needed (lease expires Mar 1, 2023)Rehab: 30-45 days max of minor rehab/renoMove-in: on or before Mar 1, 2025 (hard deadline)FinancingLoan type: FHA or FHA Streamlined 203(k) for rehab <=$35kPossible conventional loan if I seek investment from family/friendsApproval statusGoal is to get pre-approved now in advance for credibilityMy statsEmployment: Full-time at large bankIncome: low-mid 6 figuresAssets: low-mid 6 figures (including 401(k))Credit score: 800DTI: 2.5% (student loan)Thank you in advance for your support.

Im in the Metro Detroit market but while shopping Toledo I was amazed by the size and style of homes available for much less than a similar community in the Metro Detroit suburbs and it's just 45-60 minutes away.

Tarpon Springs is only about 35-45 minutes north of these areas and does not allow short-term rentals. 

If you know the game and are scaling up, I would go straight to a 4/5 bedroom. 2 and especially 3 bedroom homes are the doldrums in most markets.